735D.A. Lightner, Bilirubin: Jekyll and Hyde Pigment of Life, Progress in the Chemistry of Organic Natural Products, Vol. 98, DOI 10.1007/978-3-7091-1637-1, © Springer-Verlag Wien 2013

1. Siedel W (1939) Gallenfarbstoffe. Fortschr Chem Org Naturst 3:81 2. Fischer H, Orth H (1934) Die Chemie des Pyrrols, Bd. I. Akademische Verlagsgesellschaft,

Leipzig 3. Fischer H, Orth H (1937) Die Chemie des Pyrrols, Bd. II, Pyrrolfarbstoffe. 1. Hälfte.

Akademische Verlagsgesellschaft, Leipzig 4. Fischer H, Stern A (1940) Die Chemie des Pyrrols, Bd. II, Pyrrolfarbstoffe. 2. Hälfte.

Akademische Verlagsgesellschaft, Leipzig 5. Rüdiger W (1971) Gallenfarbstoffe und Biliproteide. Fortschr Chem Org Naturst 29:60 6. Siedel W (1940) Gallenfarbstoffe. Angew Chem 53:397 7. Siedel W (1943) Fortschritte der Chemie der Pyrrole. Angew Chem 56:185 8. Siedel W (1944) Chemie und Physiologie des Blutstoff-Abbaues. Ber Dtsch Chem Ges

77:A21 9. Fischer H, Siedel W (1947) Naturfarbstoffe II. Pyrrolsynthesen und Gallenfarbstoffe. In:

Kuhn R (Sr author) FIAT Reviews of German Science 1939-1946, Biochemistry, Part I, Office of Military Government for Germany, Field Information Agencies Technical, Dieterichsche Verlagsbuchhandlung, Wiesbaden, p 109

10. Fischer H, Plieninger H (1942) Synthese des Biliverdins (Uteroverdins) und Bilirubins, der Biliverdine IIIa und IIIa sowie der Vinylneoxanthosäure. XXXV. Mittlg. Zur Kenntnis der Gallenfarbstoffe. Hoppe-Seyler’s Z Physiol Chem 274:231

11. Fischer H, Plieninger H, Weissbarth O (1941) Über die Konstitution des Bilirubins und Über Bilirubinoide Farbstoffe. XXX. Mittlg. Zur Kenntnis der Gallenfarbstoffe. Hoppe-Seyler’s Z Physiol Chem 268:197

12. Treibs A (1971) Das Leben und Wirken von Hans Fischer. Hans-Fischer-Gesellschaft, München

13. McDonagh AF (1979) Bile Pigments: Bilatrienes and 5,15 Biladienes. In: Dolphin D (ed) The Porphyrins, vol VI. Academic Press Inc, New York, p 293

14. Lightner DA (1982) Structure, Photochemistry, and Organic Chemistry of Bilirubin. In: Heirwegh KPM, Brown SB (eds) Bilirubin, vol. I. CRC Press Inc, Boca Raton, Florida, p 1

15. Falk H (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer-Verlag, Wien

16. Антин EВ, Румянцев EB (2009) Химия билирубина его аналогов. Красанд, Москва, Руссия [Antina EV, Rumajntzev EV (2009) Chemistry of Bilirubin and Its Analogs. Krasand Publishers, Moscow]

17. Ebers G (1875) Papyros Ebers. Das Hermetische Buch Über die Artzneimittel der Alten Ägypter in Hieratischer Schrift Herausgegeben mit Inhaltsangabe und Einleitung Versehen von Georg Ebers. Mit Hieroglyphisch-lateinischem Glossar von Ludwig Stern. 2. Bände, Leipzig

18. Joachim H (1890) Papyros Ebers. Georg Reimer, Berlin

References

References736

19. Westerdorf W (1999) Handbuch der Altägyptischen Medizin. Brill, Leiden, Boston, Köln 20. Breasted JH (1930) The Edwin Smith Surgical Papyrus: Hieroglyphic Transliteration,

Translation and Commentary, vol 1. The University of Chicago Press, Chicago, Illinois 21. Renouard PV (1856) History of Medicine from Its Origin to the Nineteenth Century.

(Comegys CG trans from French). Moore, Wilstach, Keys & Co, Cincinnati, Ohio 22. Ihde AJ (1964) The Development of Modern Chemistry. Harper & Row, New York 23. Moran BT (2005) Distilling Knowledge. Alchemy, Chemistry, and the Scientific Revolution.

Harvard University Press, Cambridge, Massachusetts 24. Lavoisier AL (1789) Traité Élémentaire de Chemie, vol II. Cruchet, Paris, chap VII, p 493 25. Willstätter R (1949) Aus Meinem Leben. Verlag Chemie GmBH, Weinheim 26. Gossauer A (2003) Monopyrrolic Natural Compounds, Including Tetramic Acid Derivatives.

Prog Chem Org Nat Prod 86 27. Partington JF (1962) A History of Chemistry, vol III. Macmillan & Co, London, p 6, 468 28. Kekulé A (1861) Lehrbuch der Organischen Chemie, Bd. 1. Ferdinand Enke, Erlangen 29. Coe T (1757) A Treatise on Biliary Concretions. Or Stones in the Gall-Bladder and Ducts.

D Wilson, T Dorham, London 30. Thomson T (1817) A System of Chemistry, in Four Volumes, vol IV, 5th edn Baldwin,

Craeddock and Joy, London 31. Turner E (1835) Elements of Chemistry. Desilver, Thomas & Co, Philadelphia 32. Cadet LC (1767) Expériences sur la Bile de l’Homme et des Animaux. Mémoires de

l’Académie Royale des Sciences, Paris, p 471 33. Thomson W (1842) A Practical Treatise on the Diseases of the Liver and Biliary Passages.

Barrington ED, Haswell GD, Philadelphia, p 27 34. Vallisneri A (1733) Opere Fisico-mediche, in three volumes, vol 3. Coletti, Venice, p 594 35. von Haller A (1764) Elementa Physiologiae Corporus Humani, vol VI. Bernae Sumptibus

Societatia Typographicae, p 554 36. Macquer PJ (1778) Dictionnaire de Chymie, in four volumes, vol 2. Dichot, Paris, p 195 37. Bills CE (1935) Physiology of the Sterols, Including Vitamin D. Physiol Rev 15:1 38. Conradi BGF (1775) Dissertatio Sistens Experimenta Nonnulla cum Calculis Vesiculae

Felleae Humanae Instituta. Jena 39. Delius HF (1782) De Cholelithis. Observationes et Experimenta. Walther, Erlangen 40. Dietrich GS (1788) Dissertatio Inauguralis Medica Continens Duas Observationes Rariores

Circa Calculus in Corpore Humano Inventos, Prooemium xvi. Halle, p 66 41. Gren FAC (1789) Zerlegung Eines Gallensteins. Crells Beytr zu den Chem Ann 4:19 42. de Fourcroy AF (1789) Examen Chimique de la Substance Feuilletée et Crystalline

Contenue dans les Calculs Biliaries, et de la Natur des Concretions Cystiques Cristallisées. Ann Chim Phys, Series 1, 3:242

43. Johnson WB (1803) History of the Progress and Present State of Animal Chemistry, vol II. J Johnson, London, p 351

44. Chevreul ME (1823) De la Cholestérine. Recherches Chimiques sur les Corps Gras d’Origine Animale. Levault FG, Paris, chap IX, p 155

45. Chevreul ME (1815) Récherches Chimiques sur Plusiers Corps Gras. Annales de Chimie; ou, Recueil de Mémoires Concernant la Chimie et les Arts qui en Dépendent et Spécialement la Pharmacie, xcv, 95:5

46. Craven R (1908) Cholesterin: Some Account of Its Chemical and Biological Relations. In: Brockbank EM (ed) Dreschfield Memorial Volume. Manchester University Press, Sherbatt & Hughes Publishers to Victoria University, Manchester, p 125

47. Heuermann G (1753) Der Arzney-Gelahrheit Doktors Physiologie, dritter Theil. Friedrich Christian Pelt, Copenhagen and Leipzig, p 786

48. Tiedemann F, Gmelin L (1826) Über den Farbstoff der Galle. In: Die Verdauung nach Versuchen. K. Groos, Heidelberg, chap 10, p 79

49. Rosenfeld L (1999) Four Centuries of Clinical Chemistry. Gordon and Breach Science Publishers, Amsterdam

References 737

50. de Fourcroy AF (1801) Systéme des Connaissances Chimique, in ten volumes, vol 7. Badouin, Paris, p 44

51. Holmes FL, Levere TH, eds (2000) Instruments and Experimentation in the History of Chemistry. MIT Press, Cambridge, Massachusetts

52. Wöhler F (1828) Über Künstliche Bildung des Harnstoffs. Ann Phys Chem 88:253 53. Thenard LJ (1807) Mémoire sur la Bile; lu á l’Institut le 2 Floréal, An 13. In: Mémoires de

Physique et de Chemie de la Société d’Arcueil, Part 1. Paris, p 23 54. Thenard LJ (1807) Mémoire sur la Bile; lu á l’Institut le 2 Floréal, An 13. In: Mémoires de

Physique et de Chemie de la Société d’Arcueil, Part 1. Paris, p 40 55. Thenard LJ (1807) Mémoire sur la Bile; lu á l’Institut le 2 Floréal, An 13. In: Mémoires de

Physique et de Chemie de la Société d’Arcueil, Part 1. Paris, p 59 56. Thenard LJ (1807) Mémoire sur la Bile; Mémoires de Physique et de Chimie de la Société

d’Arcueil 64:103 57. Berzelius JJ (1806, 1808) Föreläsningar i Djukemien, 2 vols. Stockholm 58. Berzelius JJ (1812) General Views of the Composition of Animal Fluids. Medico-

Chimirgical Trans 3:198 59. Berzelius JJ (1813) A View of the Progress and Present State of Animal Chemistry,

(Brunnmark G, translation of Berzelius’ Early Book on Animal Chemistry (57) Into English). J. Shirren Publ, London, p 64

60. Berzelius JJ (1815) Übersicht der Fortschritte und des Gegenwärtigen Zustandes der Thierischen Chemie, (Sigwart GCL, trans of (59) into German). JL Schrag, Nürnberg

61. Thenard LJ (1827) Traité de Chemie Elementaire Theoretique et Pratique, 5th edn. Crochard Libraire – Editeurs des Ann Chim Phys (Paris), p 602

62. Watson CJ (1977) Historical Review of Bilirubin Chemistry. In: Berk PD, Berlin NI (eds) Chemistry and Physiology of Bile Pigments. Fogarty International Center Proceedings No. 35, DHEW Publication No. (NIH) 77-1100. US Dept of Health, Education and Welfare, Public Health Service, US National Institutes of Health, Bethesda, Maryland, p 3

63. Demarçay H (1838) Über die Natur der Galle. Liebig’s Ann Pharm 27:270 64. Loir Dr (1835) Chemische Beobachtungen Über die Harn- und Gallensteine. Ann Chem

Pharm 13:213 65. Loir Dr (1834) Observations Chimiques sur les Calculs Urinaires et Bilinaires. J Chim

Médicale Pharm Toxol 10:515 66. Liebig J, Berzelius JJ (1893) Berzelius und Liebig. Ihre Briefe von 1831-1845 mit

Erläuternden Einschaltungen aus Gleichzeitigen Briefen von Liebig und Wöhler sowie Wissenschaftlichen Nachweisen, vol I, Carrière J (ed). JF Lehmann, München u Leipzig

67. Curran JO (1846) Medical Periscope. The Physiology of Digestion as Illustrated by Modern Experiments and Observations. In: The Dublin Quarterly Journal of Medical Science; Consisting of Original Communcations, Reviews, Retrospectives and Reports, vol II. Hodges and Smith, Dublin

68. Berzelius JJ (1828) Bestandtheile der Galle. In: Jahres-Bericht Über die Fortschritte der Physischen Wissenschaften, 2nd edn, 7th volume. Heinrich Laupp, Tübingen, p 302

69. Berzelius JJ (1831) Lehrbuch der Chemie, 2nd edn, vol 4, part 1, Lehrbuch der Thier-Chemie. Arnoldischen Buchhandlung, Dresden

70. Berzelius JJ (1833) Traité de Chimie, 2e Partie-Chimie Organique, vol 7. Firmin Didot Frères, Paris

71. Berzelius JJ (1840) Lehrbuch der Chemie, 3rd edn, vol 9 (Aus der Schwedischen Handschriff des Verfassers Übersetzt von F. Wöhler), Dritte Umgearbeitete und Vermehrte Original-Auflage. Arnoldischen Buchhandlung, Dresden u Leipzig

72. Berzelius JJ (1842) Galle. In: Wagner F (ed) Handwörterbuch der Physiologie, Bd. I. F Vieweg und Sohn, Braunschweig

73. Berzelius JJ (1840) Ueber die Zusammensetzung der Galle. Ann Chem Pharm 33:139 74. Berzelius JJ (1842) Ueber die Analyse der Ochsengalle und die Characterisirenden

Eigenschaften Ihrer Bestandtheile. Ann Chem Pharm 43:1

References738

75. Berzelius JJ (1840) Ueber die Galle. J prakt Chem 20:73 76. Berzelius JJ (1842) Ueber die Galle. J prakt Chem 27:153 77. Partington JF (1962) A History of Chemistry, vol IV. Macmillan & Co, London, p 142 78. Dulk FP (1834) Alkalische Absonderungen aus d. Blute. In: Handbuch der Chemie, zum

Gebrauch bei Seinen Vorlesungen und zum Selbstunterricht, Part 2 Chemie der Organischer Körper. A Rücker, Berlin, p 461

79. Berzelius JJ (1838) Untersuchungen des Blattgrüns (Chlorophylls). Ann Chem Pharm 27:296 80. Farrar WV (1977) Edward Schunck, FRS, A Pioneer of Natural Product Chemistry. Notes

and Records of the Royal Society of London, vol 31, no 2, p 273 81. Pelletier PJ, Caventou JB (1817) Notice sur la Matière Verte des Feuilles. L. Colas, Paris 82. Liebig J (1843) Die Galle. Ann Chem Pharm 47:1 83. Thomson W (1842) A Practical Treatise on the Diseases of the Liver and Biliary Passages.

ED Barrington & Geo D Haswell, Philadelphia, p 27 84. Turner E (1835) Bile; Biliary Concretions. In: Elements of Chemistry, Including the Recent

Discoveries and Doctrines of the Science. Desilver, Thomas & Co, Philadelphia, p 620 85. Strecker A (1848) Untersuchungen der Ochsengalle. Ann Chem Pharm 65:1 86. Strecker A (1848) Untersuchungen der Ochsengalle. Ann Chem Pharm 67:1 87. Platner EA (1844) Mittheilung Über die Galle. Ann Chem Pharm 51:105 88. Platner EA (1844) Noch Etwas Über die Galle. Archive Anatomie, Physiol Wissenschaftliche

Med 2:522 89. Simon JF (1845) II. The Bile. In: Day GE (transl and ed) Animal Chemistry, with Reference

to the Physiology and Pathology of Man, in two volumes, vol I. Sydenham Society, C and J Adland, London

90. Simon JF (1840) Analysen Animalischer Substanzen in Flüssigkeiten. Archiv Pharm 74:35 91. Simon JF (1846) II. The Bile. In: Day GE (transl and ed) Animal Chemistry, with Reference

to the Physiology and Pathology of Man, in two volumes, vol II. Sydenham Society, C and J Adland, London, 43

92. Scherer JJ (1845) Ueber die Zusammensetzung und Eigenschaften der Gallenfarbstoffes. Ann Chem Pharm 53:377

93. Scherer JJ (1846) Ueber die Extractivstoffe des Harns. Ann Chem Pharm 57:180 94. Virchow R (1847) Die Pathologischen Pigmente. In: Virchow R, Reinhardt B (eds) Archiv

für pathologische Anatomie und Physiologie und für Klinische Medicin (Virchow’s Archiv), 1:379, 1:407

95. Heintz WH (1846) Notiz Über die Salpetersäure als Reagens auf Gallenbraun. In: Johannes Müller’s Archiv für Anatomie, Physiologie und Wissenschaftliche Medicin, Veit et Comp, Berlin

96. Heintz WH (1847) Notiz Über die Salpetersäure als Reagens auf Gallenbraun. Ann Physik Chem (Poggendorffs Annalen) 146:136

97. Heintz WH (1851) Ueber den in den Gallenstein Enthaltenen Farbstoff. Ann Physik Chem (Poggendorffs Annalen) 169:106

98. Lehmann CG (1850) Gallenfarbstoff. In: Lehrbuch der Physiologischen Chemie, erster Band, Zweite Auflage. Wilhelm Engelmann, Leipzig, p 320

99. Legg JW (1880) Chemistry of the Bile; The Bile Pigments. In: On the Bile, Jaundice and Bilious Diseases. D Appleton & Co, New York, chap 1 and 2, p 1, 26

100. Gmelin L (1858) Lebersecrete, Galle. In: Lehman CG, Rochleder DR (eds) Handbuch der Chemie. Universitäts-Buchhandlung von Karl Winter, Heidelberg, p 38

101. Thudichum JLW (1881) The Specific Biliary Acids of the Ox, of Man, of the Hog, and the Goose. Annals of Chemical Medicine, vol II. Longmans, Green, and Co, London, chap. XXI, p 251

102. Thudicum JLW (1863) On the Composition of Gallstones. J Chem Soc:39 103. Thudichum JLW (1863) Digest of Historical Literature. A Treatise on Gall-stones. John

Churchill and Sons, London 104. Scherer JJ (1843). Gallensteine aus Gallenfarbstoff. In: Chemische und Microskopische

Untersuchungen zur Pathologie. HL Brönner, Frankfurt, p 105

References 739

105. Hein JA (1847) Chemische Versuche Über Gallensteine und Gallenfarbstoff. J prakt Chem 40:47

106. Bley LF (1847) Chemische Prüfung von Menschlichen Gallensteinen. In: Wachenroder H, Bley LF (eds) Archiv u Zeitung des Apotheker-Vereins in Norddeutschland, vol 1. Hann’schen Hofbuchhandlung, Hannover, p 271

107. Valentiner W (1858) Zur Kenntniss der Animalischen Pigmente. Günzburg’s Zeitschr klin Med Neue Folge I, 46

108. Virchow R (1859) Auszüge und Besprechungen. 1. Valentiner, Zur Kenntniss der Animalischen Pigmente (Günsburg’s Zeitschrift für klinische Medicin. Neue Folge. I. 5. 46). In: Virchow’s Archiv Abt A Pathologische Anatomie. Pathology 17:200

109. Brücke EW (1859) Ueber Gallenfarbstoffe und ihre Auffindung. J prakt Chem 77:22 110. Schindler H (1957) Notes on the History of the Separatory Funnel. J Chem Educ 34:528 111. Virchow R (1859) Auszüge und Besprechungen. E. Bücke, Ueber Gallenfarbstoffe und ihre

Auffindung (Sitzungberichte der math. naturwiss. Classe der Wiener Akademie. Bd. XXV. S. 13). In: Virchow’s Archiv Abt A pathologische Anatomie. Pathologie 17:202

112. Saunders W (1803) A Treatise on the Structure, Economy and Diseases of the Liver, 3rd edn. William Phillips, London, p 147

113. Home E (1830) A Short Tract on the Formation of Tumours. Longmans, Rees, Orme, Brown and Green, London, Fig 3, p 28

114. Wedl C (1855) 14, Colouring Matters. In: Rudiments of Pathological Histology (Busk G, trans). Printed by Adeland JE for the Sydenham Soc, London

115. Robin C-P (1856) Zusammensetzung des Hämatoidins. J prakt Chem 67:161 116. Robin C-P (1855) Zusammensetzung des Hämatoidins. Compte Rendues t. XLI (no. 14)

p 506 117. Mulder GJ (1844) Ueber Eisenfreies Hämatin. J prakt Chem 32:186 118. Frerichs FT (1858) Klinik der Leberkrankheiten, 1st edn, vol I of 2 volumes. Friedrich

Vieweg u Sohn, Braunschweig 119. Frerichs FT (1861) Klinik der Leberkrankheiten, 2nd edn of vol I (zweite verbesserte

Auflage). Friedrich Vieweg u Sohn, Braunschweig 120. Frerichs FT (1861) A Clinical Treatment on Diseases of the Liver, vol II of 2 volumes

(Murchison C, trans from German into English). The New Sydenham Society, JW Roche, London

121. Frerichs FT (1860) A Clinical Treatment of Diseases of the Liver, vol I of 2 volumes (Murchison C, trans of improved 2nd edn of vol I of Klinik der Leberkrankheiten from German into English). The New Sydenham Society, Roche, London,

122. Pettenkofer M (1844) Notiz Über Eine Neue Reaction auf Galle und Zucker. Ann Chem Pharm 52:90

123. Kühne FW (1858) Beitrage zur Lehre vom Ikterus. In: Virchow R (ed) Virchow’s Archiv für pathologische Anatomie 15:310

124. Kühne FW (1866) Die Galle. In: Kühne’s Lehrbuch der Physiologischen Chemie. Wilhelm Engelmann, Leipzig, p 72

125. Kühne FW (1868) Die Galle. In: Kühne’s Lehrbuch der Physiologischen Chemie, Wilhelm Engelmann, Leipzig, p 88

126. Funke O (1860) Lehrbuch der Physiologie für Akademische Vorlesungen und zum Selbstudium, volume 1, 3rd revised edn. Leopold Voss, Leipzig, 245

127. Frerichs FT, Städeler G (1855) Ueber das Vorkommen von Leucin und Tyrosin in der Menschlichen Leber. Mittheilungen der Naturforschenden Gesellschaft in Zürich, vol III: 454

128. Frerichs FT, Städeler G (1856) I. Ueber das Vorkommen von Leucin und Tyrosin im Thierischen Organismus. Mittheilungen der Naturforschenden Gesellschaft in Zürich, vol IV:80

129. Frerichs FT, Städeler G (1856) Ueber die Umwandlung der Gallensäuren in Farbstoffe. Mittheilungen der Naturforschenden Gesellschaft in Zürich, vol IV:100

References740

130. Neukomm J (1860) Mittheilung aus dem Laboratorium der Prof. Städeler in Zürich (März 1860) I. Ueber die Nachweisung der Gallensäuren und die Umwandlung Derselben in der Blutbahn. Ann Chem Pharm 116:30

131. Taylor ER (1871) Prize Essay: On the Chemical Constitution of the Bile. Am Med Assoc Trans. Collins Printer, Philadelphia, p 1

132. Jaffe M (1862) Ueber die Indentität des Hämatoidins und Bilifulvins. In: Virchow R (ed), Virchow’s Archiv für pathologische Anatomie 23:192

133. Jaffe M (1864) On the Identity of Haematoidin and Bilifulvin. In: Ranking WH, Radcliffe CB (eds), The Half-Yearly Abstract of the Medical Sciences 40 (July-December):271

134. Hoppe F (1862) Über die Anwesenheit von Gallensäuren im Icterischen Harne und die Bildung des Gallenfarbstoffes. Virchows Archiv für pathologische Anatomie 24:1

135. Städeler G (1864) Ueber die Farbstoff der Galle. Ann Chem Pharm 132:328 136. Holm F, Städeler G (1867) Untersuchung Über das Hämatoidin. J prakt Chem 100:142 137. Salkowski EL (1868) Hoppe-Seyler’s Medicinisch-Chemische Untersuchungen, herausgeg.

von Hoppe-Seyler. Berlin Heft 3:436 138. Preyer WT (1871) Die Blutkrystalle. Mauke’s Verlag, Jena, p 185 139. Wagner E (1876) A Manual of General Pathology (van Duyn J, Seguin EC, trans, from 6th

German edn into English). William Wood & Co, New York 140. Kingzett CT (1878) Bile Pigments. In: Animal Chemistry or the Relations of Chemistry to

Physiology and Pathology. Longmans, Green and Co, London, p 100 141. Hermann L (1883) Die Bildung der Specifischen Gallenbestandtheile. In: Vogel FWC,

Handbuch der Physiologie, Fünfter Band, 1. Theil. Leipzig, p 231 142. Ewald CA (1891) Lectures on the Diseases of the Digestive Organs, vol I (Saundby R, trans,

into English from 3rd German edn, 1890). The New Sydenham Society, London, p 133 143. Landois L (1892) Constituents of the Bile. In: A Text-book of Human Physiology, 4th edn.

(Stirling W, trans from 7th German edn, with additions). P Blakiston, Son & Co, Philadelphia, 333

144. Cohen JB (1919) The Proteins. In: Organic Chemistry for Advanced Students, part III, Synthesis, 2nd edn, 2nd impression. Longmans, Green & Co, New York

145. Fischer H, Reindel F (1923) Über Hämatoidin. Hoppe-Seyler’s Z physiol Chem 127:299 146. Rich AR (1925) The Formation of Bile Pigment. Physiol Rev 5:182 147. Rocke AJ (2010) Image and Reality. Kekulé, Kopp and the Scientific Imagination.

University of Chicago Press, Chicago and London 148. Everts S (2010) When Science Went International. Chem Eng News, 6 September 2010,

88:60 149. Kauffman GB, Adloff J-P (2010) The 150th Anniversary of the First International Congress

of Chemists, Karlsruhe, Germany, September 3-5, 1860. Chem Educator 15:309 150. Maly RL (1864) Vorläufige Mittheilungen Über die Chemische Natur der Gallenfarbstoffe.

Anzeiger der kaiserlichen Akademie der Wissenschaften I:81 151. Städeler G (1860) Ueber das Tyrosin. Ann Chem Pharm 116:57 152. Thudichum JLW (1868) Chemische Untersuchungen Über die Gallenfarbstoffe. J prakt

Chem 104:193 153. Heynsius A, Campbell JFF (1871) Die Oxydationsproducte der Gallenfarbstoffe und ihre

Absorptionstreifen. In: Pflüger EWF, Archiv für die Gesammte Physiologie der Menschen und Thiere, vierter Jahrgang, erstes Heft. Max Cohen & Sohn, Bonn

154. Wood ES (1873) Report on Medical Chemistry. In: Warren JC, Dwight T, Draper FW (eds) The Boston Medical and Surgical Journal, vol 88, David Clapp & Son, Boston, p 14

155. Lightner DA, McDonagh AF (1984) Molecular Mechanisms of Phototherapy for Neonatal Jaundice. Acc Chem Res 17:417

156. Lightner DA, McDonagh AF (1985) Like a Shrivelled Blood Orange. Bilirubin, Jaundice and Photo therapy. Pediatrics 75:443

157. Lightner DA, McDonagh AF (1988) Phototherapy and the Photobiology of Bilirubin. Sem Liv Dis 8:272

References 741

158. Thudichum JLW (1875) Further Researches on Bilirubin and its Compounds. In: Papers Read Before the Chemical Society, J Chem Soc 28:389

159. Thudichum JLW (1876) On Some Reactions of Biliverdin. The Chemical News 33:198 (12 May)

160. Thudichum JLW (1876) On Some Reactions of Biliverdin. In: Papers Read Before the Chemical Society, J Chem Soc 30:27

161. Thudichum JLW (1876) Offenes Schreiben an die kaiserliche Akademie der Wissenschaft zu Wien Enthaltend eine Beluchtung der Untersuchen Über die Gallenfarbstoffe von Richard Maly in Graz. In: Pflüger’s Archiv Anat Physiol (Pflüger’s Archiv Eur J Physiol) 13:213

162. Thudichum JLW (1876) State of Animal Chemistry in Austria. (Open Letter to the Imperial Academy of Sciences at Vienna, Containing an Examination of the Researches on the Colouring Matter of the Bile, by Richard Maly of Graz.) The Chemical News 32/33:154 (April)

163. Thudichum JLW (1884) A Treatise on the Chemical Consitution of the Brain. Balliere, Tindal, and Cox, London

164. Maly RL (1864) Vorläufige Mittheilungen Über die chemische Natur der Gallenfarbstoffe. Ann Chem Pharm 132:127

165. Maly RL (1864) Über die Chemische Natur der Gallenfarbstoffe. In: Sitzungberichte der Mathematisch-Naturwissenschaftlichen Classe der kaiserlichen Akademie der Wissenschaften, Herr Prof R Maly, Assistent der Physiologie und der Grazer Universität Übersendet Einige “Vorläufige Mittheilungen Über die Chemische Natur der Gallenfarbstoffe”, XIII. Sitzung vom 12 Mai 1864, vol 49, KK Hof- und Staatsdruckerei, Wien, p 463

166. Maly RL (1868) Untersuchungen Über die Gallenfarbstoffe. J prakt Chem 104:28 167. Maly RL (1868) Intersuchungen Über die Gallenfarbstoffen. In: Sitzungberichte der

Mathematisch-Naturwissenschaftlichen Classe der kaiserlichen Akademie der Wissenschaften, Herr Prof R Maly Übermittlet die Erste Abtheilung Seiner “Untersuchungen Über die Gallenfarbstoffe”, IV. Sitzung vom 6 Feb 1868, vol 57, Heft IV, KK Hof- und Staatsdruckerei, Wien, p 227

168. Ma J, Yan F, Wang C, Chen J (1990) Addition of Sodium Bisulfite to Biliverdin. Chin Chem Lett 8:23

169. McDonagh AF (2010) Personal Communication 170. Senge MO, Ma J, McDonagh AF (2001) Sodium Etiobilirubin-IVg-C10-sulfonate: A

Highly Solvated Bile Pigment Structure Containing Two Different Non-ridge-tile Conformers in the Unit Cell. Bioorg Med Chem Lett 11:875

171. Maly R (1874) Untersuchungen Über die Gallenfarbstoffe. In: Sitzungberichte der Mathematisch-Naturwissenschaftlichen Classe der kaiserliche Akademie der Wissenschaften, Herr Prof R Maly, Assistent der Physiologie und der Grazer Universität Übersendet Einige “Vorläufige Mittheilungen Über die Chemische Natur der Gallenfarbstoffe”, XVII. Sitzung vom 9 July 1874, vol 70, KK Hof- und Staatsdruckerei, Wien, p 72

172. Maly RL (1875) Untersuchungen Über die Gallenfarbstoffe. Ann Chem Pharm 175: 76 173. Falk H (1989) The Chemistry of Linear Oligopyrroles and Bile Pigments. Springer-Verlag,

Wien, Fig 4-6, p 47 174. Maly RL (1869) Untersuchungen der Gallenfarbstoffen. In: Sitzungberichte der

Mathematisch-Naturwissenschaftlichen Classe der kaiserliche Akademie der Wissenschaften, Herr Prof R Maly, Assistent der Physiologie und der Grazer Universität Übersendet Einige “Vorläufige Mittheilungen Über die Chemische Natur der Gallenfarbstoffe”, IX. Sitzung vom 1 April 1869, I. Untersuchungen der Gallenfarbstoffen von Prof R Maly in Olmütz, vol 59, Heft 4, KK Hof- und Staatsdrukerei, Wien, p 509

175. Maly RL (1872) Künstliche Umwandlung von Bilirubin in Harnfarbstoff. Ann Chem Pharm 161:368

References742

176. Maly RL (1872) Untersuchungen Über die Gallenfarbstoffe. III. Umwandlung von Bilirubin in Harnfarbstoff. Ann Chem Pharm 163:77

177. Maly RL (1875) Untersuchungen Über die Gallenfarbstoffe. In: Sitzungberichte der Mathematisch-Naturwissenschaftlichen Classe der kaiserlichen Akademie der Wissenschaften, Herr Prof R Maly, Assistent der Physiologie und der Grazer Universität Übersendet Einige “Vorläufige Mittheilungen Über die Chemische Natur der Gallenfarbstoffe”, III. Sitzung vom October 1875, vol 72, KK Hof- und Staatsdruckerei, Wien

178. Maly RL (1876) Untersuchungen Über die Gallenfarbstoffe. Ann Chem Pharm 18:106 179. Watts H (1868) A Dictionary of Chemistry, vol V. Longman’s Green and Co, London,

p 377 180. Hoppe-Seyler F (1862) Ueber das Verhalten des Blutstoffes im Spectrum des Sonnenlichtes.

Virchow’s Archiv pathol Anat klin Med 23:446 181. Kohlrausch WG (1874) An Introduction to Physical Measurements. (Walter TH, Proctor

HR, trans from the 7th German edn into English), D Appleton and Company, New York, p 97, 231

182. Beer A (1852) III. Bestimmung der Absorbtion des Rothen Lichts in Farbigen Flüssigkeiten. Poggendorff’s Ann Phys Chem 86:78

183. Bunsen R, Roscoe H (1857) IV. Photochemische Untersuchungen. Poggendorff’s Ann Phys Chem 13:235

184. Rinsler MG (1981) Spectroscopy, Colorimetry, and Biological Chemistry in the Nineteenth Century. J Clin Pathol 34:287

185. Jaffe M (1869) Zur Lehre von den Eigenschaften und der Abstammung der Harnpigmente. Virchow’s Archiv pathol Anatomie klin Medicin 47:405

186. Thudichum JLW (1872) A Manual of Chemical Physiology. William Wood & Company, New York, p 71

187. Thudichum JLW (1896) Ueber die Reactionen des Bilirubins mit Jod und Chloroform. J prakt Chem 53:314

188. Thudichum JLW (1897) Das Sogenannte Urobilin und Damit in Verbindung Gesetzen Physiologischen und Pathologischen Hypothesen. Virchow’s Archiv pathol Anat klin Med 150:586

189. Thudichum JLW (1898) Ueber das Urobilin. Virchow’s Archiv pathol Anat klin Med 153:154

190. Thudichum JLW (1899) Ueber den Chemischen Process der Gallensteinkrankheit beim Menschen und in Thieren. Virchow’s Archiv pathol Anat klin Med 156:384

191. Thudichum JLW (1900) Einige Wissenschaftliche und Ethische Fragen der Biologischen Chemie. J prakt Chem 61:568

192. Grimm F (1893) Ueber Urobilin im Harne. Virchow’s Archiv pathol Anat klin Med 132:246

193. Thudichum JLW (1877) A Treatise on the Pathology of the Urine, 2nd edn. J&A Churchill, London

194. Hopkins FG, Garrod AE (1898) On Urobilin. Part II. The Per-centage Composition of Urobilin. J Physiol 22:451

195. Garrod AE, Hopkins FG (1896) On Urobilin. Part I. The Unity of Urobilin. J Physiol 20:112

196. Jolles A (1894) Beitrage zur Kenntnis der Gallen und Über Eine Quantitative Methode zur Bestimmung des Bilirubins in der Menschlichen und Thierischen Galle. Pflüger’s Archiv Physiol (Eur J Physiol) 57:1

197. Jolles A (1899) Ueber die Reaction des Bilirubins mit Jod und Chloroform. J prakt Chem 59:308

198. Küster W (1899) Beiträge zur Kenntniss der Gallenfarbstoffe. I. Hoppe-Seyler’s Z physiol Chem 26:314

199. Küster W (1899) Ueber den Blut- und den Gallen-farbstoff. Ber Dtsch Chem Ges 32:677

References 743

200. Breathnach CS (2001) Johann Ludwig Wilhelm Thudichum 1829-1901, Bane of the Protagonizers. History of Psychiatry vol XII:283

201. Gamgee A (1893) A Text-book of the Physiological Chemistry of the Animal Body, includ-ing an Account of the Chemical Changes Occurring in Disease. II. MacMillan & Co, London and New York, p 315

202. Kekulé A (1859) Lehrbuch der Organischen Chemie, vol 1. Ferdinand Enke, Erlangen 203. Rambert PJ (2010) Imagination in Chemistry. Science 329:280 (a review of ref 145) 204. Nencki M, Sieber N (1888) Über das Hämatoporphyrin. Monatsh Chem 9:115 205. Nencki M, Sieber N (1888) Ueber des Hämatoporphyrin. (Naunyn and Schmiedeberg’s)

Archiv exp Pathol Pharmacol 24:430 206. Raoult FM (1899) The General Law of Freezing Solvents. In: Ames JS (ed) Harper’s

Scientific Memoirs IV. The Modern Theory of Solutions (Jones HC, transl and ed, from the original French: Ann Chim Phys 1884 2:66). Harper & Brothers, New York and London

207. Beckmann E (1905) Modifikation des Thermometers für die Bestimmung von Molekulargewichten und Kleinen Temperatur Differenzen. Z Phys Chem 51:329

208. Nencki M, Rotschky A (1889) Zur Kenntniss des Hämatoporphyrins und des Bilirubins. Monatsh Chem 10:568

209. Rast K (1922) Mikro-Molekulargewichts-Bestimmung im Schmelzpunktsapparat. Ber Dtsch Chem Ges 55:1051

210. Abel JJ (1890) Bestimmung des Moleculargewichtes der Cholalsäure, des Cholesterins und des Hydrobilirubins nach der Raoult’schen Methode. Monatsh Chem 11:61

211. Teeple JE (1903) On Bilirubin, the Red Coloring-Matter of the Bile. A Dissertation submit-ted to the University Faculty for the Degree of Doctor of Philosophy at Cornell University, Ithaca, New York

212. von Zumbusch LR (1901) Ueber das Bilifuscin. Hoppe-Seyler’s Z Physiol Chem 31:446 213. Orndorff WR, Teeple JE (1901) On Bilirubin, the Red Coloring-matter of the Bile. Amer

Chem J 26:86 214. Orndorff WR, Teeple JE (1905) On Bilirubin, the Red Coloring-matter of the Bile. Amer

Chem J 32:215 215. Küster W (1902) Beiträge zur Kenntniss der Gallenfarbstoffe. III. Ber Dtsch Chem Ges

35:1268 216. Küster W (1894) Ueber Chlorwasserstoffsaures und Bromwasserstoffsaures Hämatin. Ber

Dtsch Chem Ges 27:572 217. Küster W. Haas K (1904) Beiträge zur Kenntniss des Hämatins. Ber Dtsch Chem Ges

37:2470 218. Küster W (1904) Haematin. J Chem Soc Abst 86:647 219. Hünefeld FL (1840) Der Chemismus in der Thierischen Organisation. Brockhaus, Leipzig 220. Hoppe-Seyler F (1864) Ueber die Chemischen und Optischen Eigenschaften des

Blutfarbstoffs. Virchow’s Archiv: An Internat J Pathol 29:233 221. Reichert ET, Brown AP (1909) The Differentiation and Specificity of Corresponding

Proteins and Other Vital Substances in Relation to Biological Classification and Organic Evolution. The Crystallography of Hemoglobins. Carnegie Institution of Washington, DC

222. Reichert KE (1849) Beobachtungen Über eine Eiweissartige Substanz in Krystallform. Müller’s Archiv Anat Physiol Wiss Med:198

223. Funke O (1851) Ueber das Milzvenenblut. Z rationelle Med NF 1:172 224. Teichmann L (1853) Ueber die Krystallisation der Organischen Bestandtheile des Bluts. Z

rationelle Med für Henle und Pfeuffer 3:375; Ueber das Hämatin ibid 8:141 (1857) 225. Hoppe-Seyler F (1864) Ueber die Chemischen und Optischen Eigenschaften des

Blutfarbstoffs. Virchow’s Archiv: An Internat J Pathol 29:597 226. Mulder GJ (1844) Ueber Eisenfreies Hämatin. J prakt Chem 32:186 227. Hoppe-Seyler F (1871) Beiträge zur Kenntniss des Blutes des Menschen und der

Wirbelthiere (Schluss). Medicin-chemische Untersuchungen, herausgeben von Dr. Felix Hoppe-Seyler, erstes Heft, August Hirschwald, Berlin, p 523

References744

228. Hoppe-Seyler F (1874) Einfache Darstellung von Harnfarbstoff aus Blutfarbstoffs. Ber Dtsch Chem Ges 7:1065

229. Nencki M, Sieber N (1884) Untersuchungen Über den Blutfarbstoff. Ber Dtsch Chem Ges 17:2267

230. Nencki M, Sieber N (1884) Untersuchungen Über den Blutfarbstoff. (Naunyn and Schmiedeberg’s) Archiv exper Pathol Pharm 18:401

231. Runge FF (1834) Ueber Einige Produkte der Steinkohlendestillation. Poggendorff’s Ann Phys 31:65; ibid 32:308

232. Anft B (1955) Friedlieb Ferdinand Runge: A Forgotten Chemist of the Nineteenth Century. J Chem Educ 32:566

233. Anderson HJ (1995) From Dippel to Du Pont. J Chem Educ 72:875 234. Anderson Th (1858) Ueber die Producte der Trockenen Distillation Thierische Matieren.

Ann Chem Pharm 105:335 235. Anderson Th (1846) Ueber Picolin; eine Neue Basis aus dem Steinkohlen-Theeröl. Ann

Chem Pharm 60:86 236. Schwanert H (1860) Ueber Einige Zersetzungsproducte der Schleimsäure. Ann Chem

Pharm 116:257 237. Baeyer A (1870) Ueber die Wasserentziehung und ihre Bedeutung für das Pflanzenleben

und die Gährung. Ber Dtsch Chem Ges 3:63 238. Fittig R (1871) Ueber die Constitution der Sogenannten Kohlenhydrate. LF Fues, Tübingen 239. Baeyer A (1870) Reduction des Isatins zu Indigblau. Ber Dtsch Chem Ges 3:514 240. Cason J, Rapoport H (1950) Laboratory Text in Organic Chemistry. Prentice-Hall, Inc,

Englewood Cliffs, New Jersey, p 186 241. Nencki M, Sieber N (1886) Ueber das Hämin. (Naunyn and Schmiedeberg’s) Archiv exp

Pathol Pharmacol 20:325 242. Küster W (1896) Beiträge zur Kenntniss des Hämatins. Ber Dtsch Chem Ges 29:821 243. Küster W (1897) Ueber Oxydationsproducte des Hämatoporphyrins und die

Zusammensetzung des nach Verschiedenen Methoden Dargestellen Hämins. Ber Dtsch Chem Ges 30:105

244. Küster W (1897) Ueber ein Spaltungsproduct des Gallenfarbstoffs, die Biliverdinsäure. Ber Dtsch Chem Ges 30:1831

245. Lassaigne JL (1843) Mémoire sur un Procédé Simple pour Constater las Présence d’Azote dans des Quantités Minimes de Matière Organique. Comptes Rendues Hebdomadaires des Sé Acad Sci 16:387

246. Lassaigne JL (1843) Nachweisung Ausserst Geringer Mengen Stickstoff in Organischen Matieren. Ann Chem Pharm 48:367

247. Gower RP, Rhodes IP (1969) A Review of Techniques in the Lassaigne Sodium Fusion. J Chem Educ 46:606

248. Küster W (1899) Spaltungsproducte des Hämatins. Hoppe-Seyler’s Z Physiol Chem 28:1 249. Küster W, Kölle M (1899) Ueber Darstellung und Spaltungsproducte des Hämatoporphyrins.

Hoppe-Seyler’s Z Physiol Chem 28:34 250. Küster W (1900) Spaltungsprodukte des Hämatins (II. Mittheilung). Hoppe-Seyler’s Z

Physiol Chem 29:185 251. Küster W (1900) Ueber die Constitution der Hämatinsäure. Ber Dtsch Chem Ges 33:3021 252. Küster W (1901) Ueber die Constitution des Hämatinsäuren. Liebig’s Ann Chem 315: 174 253. Fittig R, Glaser F (1899) Umlagerung Zweibasische Ungesättiger Säuren. III.

Aethylitaconsäure und Isomere Säuren. Liebig’s Ann Chem 304:178 254. Bischoff CA (1890) Weitere Beiträge zur Kenntniss der Homologen der Maleïnsäuregruppe.

Ber Dtsch Chem Ges 23:3413 255. Bischoff CA (1891) Weitere Beiträge zur Kenntniss der Fumarsäurereihe. Ber Dtsch Chem

Ges 24:2001 256. Fittig R, Landolt A (1877) Untersuchungen Über die Ungesättigen Säuren. 4) Beiträge zur

Kenntnis der Additionsproducte aus Ita-, Citra- und Mesaconsäure. Liebig’s Ann Chem 188:71

References 745

257. Fittig R, Jayne HW (1882) Ueber das Phenyl-Butyrolacton und die Phenyl-Paraconsäure. Liebig’s Ann Chem 216:97

258. Fittig R (1889) Ueber Lactonsäure, Lactone und Ungesättigte Säuren. Liebig’s Ann Chem 255:1

259. Aronheim B (1874) Synthese des Phenylbutylens. Liebig’s Ann Chem 171:219 260. Fittig R, Penfield SL (1883) Ueber die Phenylhomoparaconsäure. Liebig’s Ann Chem

216:119 261. Fittig R, Delisle A (1889) Propionaldehyd und Bersteinsäure. Liebig’s Ann Chem 255:56 262. Fittig R, Parker G (1892) Ueber die Condensation der Brenztraubensäure mit Zweibasischen

Säuren. Liebig’s Ann Chem 267:204 263. Michael A, Tissot G (1891) Zur Kenntniss der Homologen der Aepfelsäure. Ber Dtsch

Chem Ges 24:2544 264. Michael A, Tissot G (1892) Beiträge zur Kenntniss Einiger Homologen der Aepfelsäure.

J prakt Chem 46:285 265. Bischoff CA, Voit E (1890) Ueber die Beziehungen der Beiden Symmetrischen

Dimethylbernsteinsäuren zur Pyrocinchonsäure. Ber Dtsch Chem Ges 23:644 266. Bischoff CA (1891) Weitere Beiträge zur Kenntniss der Substituirten Bernsteinsäuren. Ber

Dtsch Chem Ges 24:1064 267. Hilditch TP (1911) A Concise History of Chemistry. D Van Nostrand Co, New York 268. von Richter V (1916) Organic Chemistry, or Chemistry of the Carbon Compounds, Vol I,

Chemistry of the Aliphatic Series (Spielman PE, trans and rev from German edn), P. Blakiston’s Son & Co, Philadelphia

269. Liebig J, Poggendorff JC, Wöhler Fr (1859) Handwörterbuch der Reinen und Angewandten Chemie, zweite Auflage, zweiter Band, zweite Abteilung (neu bearbeitet in Verbindung mit mehreren Gelehrten und redigirt von Fehling H), Friedrich Vieweg u Sohn, Braunschweig

270. Frankland E, Duppa BF (1866) Synthetische Untersuchungen Über Aether. Ann Chem Pharm 138: 204, 328

271. Frankland E, Duppa BF (1868) Synthetische Untersuchungen Über Aether. Ann Chem Pharm 145:78

272. Geuther A (1883) Ueber die Constitution des Acetessigesters (Aethyldiacetsäure) und Über Diejenige des Benzols. Liebig’s Ann Chem 219:119

273. Geuther A (1885) Zur Geschichte des Acetylacetessigäthers. Liebig’s Ann Chem 227:383 274. Baeyer A (1885) Ueber die Synthese des Acetessigäthers und des Phloroglucins. Ber Dtsch

Chem Ges 18:3454 275. Nef JU (1891) Zur Kenntniss des Acetessigäthers. Liebig’s Ann Chem 266:52 276. Claisen L, Lowman O (1887) Ueber eine Neue Bildungsweise des Benzoylessigäthers. Ber

Dtsch Chem Ges 20:651 277. Claisen L (1892) Ueber die Constitution des Acetessigäthers und der Sogenannten

Formylverbindungen der Säuräther und Ketone. Ber Dtsch Chem Ges 25:1776 278. Claisen L (1905) Ueber den Verlauf der Natracetessigester – Synthese. Ber Dtsch Chem

Ges 38:709 279. Dessaigne M (1858) On a New Acid Obtained by Oxidation of Malic Acid. The Chem Gazz

382:341 280. Conrad M (1880) Synthesen Mittelst Malonsäureester; 1. Darstellung des Malonsäureesters

von M. Conrad und C.A. Bischoff. Liebig’s Ann Chem 204:121 281. Zelinsky N (1887) Ueber eine Bequeme Darstellungsweise von a-Brompropionsäureester.

Ber Dtsch Chem Ges 20:2026 282. Nencki M, Zaleski J (1900) Untersuchungen Über den Blutfarbstoff. Hoppe-Seyler’s Z

Physiol Chem 30: 384 283. Auwers K (1891) Ueber Synthesen Alkylirter Tricarballylsäuren und Anderer Mehrbasischer

Fettsäuren. Ber Dtsch Chem Ges 24:307 284. Auwers K, Köbner E, von Meyenburg F (1891) Synthesen Mehrbasischer Fettsäuren. Ber

Dtsch Chem Ges 24:2887

References746

285. Nencki M, Zaleski J (1901) Ueber die Reductionsproducte des Hämins durch Jodwasserstoff und Phosphoniumjodid und Über die Constitution des Hämins und Seiner Derivate. Ber Dtsch Chem Ges 34:997

286. Nencki M, Marchelewski L (1901) Zur Chemie des Chlorophylls. Abbau des Phyllocyanins zum Hämopyrrol 34:1687

287. Zaleski J (1902) Untersuchungen Über das Mesoporphyrin. Hoppe-Seyler’s Z Physiol Chem 37:54

288. Küster W (1902) Beiträge zur Kenntniss des Hämatins. Ber Dtsch Chem Ges 35:2948 289. Küster W (1904) Über die nach Verschiedenen Methoden Hergestellten Hämine, das

Dehydrochlorhämin und das Hämatin. Hoppe-Seyler’s Z Physiol Chem 40:391 290. Küster W (1905) Beiträge zur Kenntniss des Hämatins. Hoppe-Seyler’s Z Physiol Chem

44:391 291. Küster W (1906) Ueber die Constitution der Hämatinsäuren. Liebig’s Ann Chem 345:1 292. Küster W, Haas K (1906) Ueber die Constitution des Hämopyrrols. Liebig’s Ann Chem

346:1 293. Plancher G, Cattadori F (1903) Sull’ ossidazione del Dimetilpirrolo Asimmetrico. Atti della

Accademia nationale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti 12:10

294. Plancher G, Cattadori F (1903) Sull’ Ossidazione del Dimetilpirrolo Asimmetrico. Gazz Chim Ital 33:402

295. Schmidt J (1904) Die Chemie des Pyrrols und Seiner Derivate. Verlag von Ferdinand Enke, Stuttgart

296. Küster W (1907) Ueber das Hämopyrrol. Ber Dtsch Chem Ges 40:2017 297. Küster W, Haas K (1906) Constitution of Haemopyrrole. J Chem Soc Abst 90:693 298. Harries C (1920) Oskar Piloty. Ber Dtsch Chem Ges 53:152 299. Remarque EM (1929) Im Westen Nichts Neues. Propyläen-Verlag, Berlin, p 91, 260 300. Remarque EM (1958) All Quiet on the Western Front. (Wheen AW, trans into English for

Little, Brown & Co, 1929, 1930). Ballentine Books, Random House, New York, p 87, 263 301. Piloty O, Thannhauser SJ (1912) Über die Konstitution des Blutfarbstoffs. Liebig’s Ann

Chem 390:191 302. Piloty O, Thannhauser SJ (1912) Dehydro-bilinsäure, ein Gefärbtes Oxydations-Produkt

der Bilinsäure. Ber Dtsch Chem Ges 45:2393 303. Piloty O (1909) Ueber den Farbstoff des Blutes. Liebig’s Ann Chem 366:237 304. Piloty O (1911) Sur le Coulerant du Sang. Le Moniteur Scientifique du Docteur Quesnville.

J Sciences Pures Appliquées, Compte Rendus Académies Sociétés Savantes T4:711 305. Hahn O (1970) My Life. (Kaiser E, Wilkins E, trans into English of Mein Leben). Herder

and Herder, New York, p 95 306. Piloty O, Merzbacher S (1909) Ueber die Sogenannte Hämatopyrrolidinsäure. Ber Dtsch

Chem Ges 42:3253 307. Piloty O, Merzbacher S (1909) Über eine Neue Aufspaltung des Hämatoporphyrin. Ber

Dtsch Chem Ges 42:3258 308. Piloty O, Quitmann E (1909) Über die Konstitution des Hämopyrrols und des

Hämopyrrolcarbonsäure. Ber Dtsch Chem Ges 42:4693 309. Küster W (1909) Beiträge zur Kenntniss des Hämatins. (Bemerkunges zu O. Pilotys Arbeit

Über den Farbstoff des Blutes und Über die Oxydation des Hämatoporphyrins). Hoppe-Seyler’s Z Physiol Chem 61:164

310. Küster W (1908) Beiträge zur Kenntniss des Hämatins. Hoppe-Seyler’s Z Physiol Chem 55:505

311. Goldmann H, Hetper J, Marchelewski L (1905) Studien Über den Blutstoff. V. Vorläufige Mitteilung. Hoppe-Seyler’s Z Physiol Chem 45:176

312. Piloty O (1910) Synthese von Pyrrolderivaten: Pyrrole aus Succinylobernstein-säureester, Pyrrole aus Azinen. Ber Dtsch Chem Ges 43:489

313. Piloty O, Quitmann E (1910) Über die Konstitution der Gefärbten Komponente des Blutfarbstoffes. Liebig’s Ann Chem 377:314

References 747

314. Piloty O, Dormann E (1912) Über die Konstitution des Blutfarbstoffs. Liebig’s Ann Chem 388:313

315. Piloty O, Wilke K (1912) Über das a,b-Dimethylpyrrol. Ber Dtsch Chem Ges 45:2586 316. Dennstedt M (1889) Ueber die c-Dimethylpyrrole. Ber Dtsch Chem Ges 22:1920 317. Dennstedt M (1889) Ueber die im Dippel’schen Oel Enthaltenen c-Dimethylpyrrole. Ber

Dtsch Chem Ges 22:1924 318. Weidel H, Ciamician GL (1880) Studien Über Verbindungen aus dem Animalischen Theer.

Ber Dtsch Chem Ges 13:65 319. Knorr L (1884) Synthese von Pyrrolderivaten. Ber Dtsch Chem Ges 17:1635 320. Knorr L (1886) Synthetische Versuche mit dem Acetessigester. Überführung des

Diacetbernsteinsäure-esters und des Acetessigesters in Pyrrol-Derivate; Einwirkung von Ammoniak und Primären Aminen auf den Diacetbernsteinsäure-ester. Überführung des Acetessigesters in Pyrrole-Derivate. Liebig’s Ann Chem 236:290

321. Paal C (1885). Synthese von Thiophen- und Pyrrolderivaten. Ber Dtsch Chem Ges 18:367 322. Knorr L, Lange H (1902) Ueber die Bildung von Pyrrolderivaten aus Isonitrosoketonen.

Ber Dtsch Chem Ges 35:2998 323. Knorr L, Hess K (1911) Synthese des 2,4-Dimethyl-3-äthyl-pyrrols, ein Beitrage zur

Lösung der Konstitution des Hämopyrrols. Ber Dtsch Chem Ges 44:2758 324. Knorr L (1885) Einwirkung des Diacetbernsteinsäureesters auf Ammoniak und Primäre

Aminbasen. Ber Dtsch Chem Ges 18:299 325. Küster W (1909) Beiträge zur Kenntniss der Gallenfarbstoffe. Ueber Bilirubin, Biliverdin

und ihre Spaltungsprodukte. Hoppe-Seyler’s Z Physiol Chem 59:63 326. Küster W (1906) Beiträge zur Kenntniss der Gallenfarbstoffe. Hoppe-Seyler’s Z Physiol

Chem 47:294 327. Piloty O (1913) Bemerkungen zu der Mitteilung der HHrn. Hans Fischer und Heinrich

Röse im 3 Heft dieser Berichte. Ber Dtsch Chem Ges 46:1000 328. Piloty O, Stock J, Dormann E (1914) Zur Konstitution des Blutfarbstoffs; Dipyrrylmethan-

Derivate mit Farbstoff-Charakter. Ber Dtsch Chem Ges 47:400 329. Piloty O, Stock J. Dormann E (1914) Zur Konstitution des Blutfarbstoffs; Dipyrrylmethan-

Derivate mit Farbstoff-Character. II. Ber Dtsch Chem Ges 47:1124 330. Piloty O, Krannich W, Will H (1914) Zur Konstitution des Blutfarbstoffs: Dipyrrylmethan-

Derivate mit Farbstoff-Charakter. III. Ber Dtsch Chem Ges 47:2531 331. Piloty O, Stock J, Dormann E (1914) Über die Konstitution des Blutfarbstoffs. Über das

Hämopyrrol and die Phonopyrrolcarbonsäuren. Liebig’s Ann Chem 406:342 332. Piloty O, Fink H (1912) Über die Molgröße des Hämins und Hämoglobins. Ber Dtsch

Chem Ges 45:2495 333. Piloty O, Dormann E (1912) Über die Phonopyrrol-carbonsäure und Ihre Begleiter. Ber

Dtsch Chem Ges 45:2592 334. Piloty O, Hirsch P (1912) Über die Hämatopyrrolidinsäure. Ber Dtsch Chem Ges 45:2595 335. Piloty O, Blömer A (1912) Über Eine Synthese des Hämopyrrol b. Ber Dtsch Chem Ges

45:3749 336. Piloty O, Stock J (1912) Über die Konstitution des Blutfarbstoffs. IV. Über Hämopyrrol.

Liebig’s Ann Chem 392:215 337. Piloty O, Dormann (1913) Über die Sauren Spaltstücke des Hämins. Preliminary

Communication. Ber Dtsch Chem Ges 46:1002 338. Piloty O, Stock J (1913) Über das Hämopyrrol. Ber Dtsch Chem Ges 46:1008 339. Piloty O, Wilke K (1913) Tetramethyl-pyrrindochinon und Andere: Derivate des Dimethyl-

2.3-pyrrols. Ber Dtsch Chem Ges 46:1597 340. Piloty O, Fink H (1913) Über das Phonoporphyrin, ein Neues Spaltstück des Hämins. Ber

Dtsch Chem Ges 46:2020 341. Piloty O, Will H (1913) Über Kondensation von Oxalester mit Acetyl-pyrrolen. Ber Dtsch

Chem Ges 46:2607 342. Piloty O, Hirsch P (1913) Pyrrol-Synthesen aus Aminoketonen mit Ketonen und

Ketonsäureestern. Liebig’s Ann Chem 395:63

References748

343. Willstätter R, Fischer M (1913) Untersuchungen Über den Blutfarbstoff. I. Mitteilung. Über den Abbau des Hämins zu Porphyrinen. Hoppe-Seyler’s Z Physiol Chem 87:423

344. Willstätter R, Stoll A (1913) Untersuchungen Über Chlorophyll. Julius Springer, Berlin 345. Zeile K (1946) Das Lebenswerk Hans Fischers. Naturwissenschaften 33:289 346. Treibs A (1946) In Memoriam. Hans Fischer. Z Naturforsch 1:476 347. Wieland H (1950) Hans Fischer und Otto Hönigschmid zum Gedächtnis. Angew

Chem 62:1 348. Fischer H (1912) Über Urobilin und Bilirubin. Habilitationsschrift zu Erlangung der Venia

Legendi. München, Kgl Hof. und Univ. Buchdruckerei Dr. C Wolf & Sohn 349. Fischer H (1911) Zur Kenntniss des Gallenfarbstoffs. I. Mittlg. Hoppe-Seyler’s Z Physiol

Chem 73:204 350. Fischer H, Meyer-Betz F (1911) Zur Kenntniss des Gallenfarbstoffs. II. Mittlg. Über das

Urobilinogen des Urins und das Wesen der Ehrlich’schen Aldehyd-Reaktion Hoppe-Seyler’s Z Physiol Chem 75:232

351. Fischer H, Meyer P (1911) Zur Kenntniss des Gallenfarbstoffs. III. Mittlg. Über Hemibilirubin und die bei der Oxydation des Hemibilirubins Entstehenden Spaltprodukte. Hoppe-Seyler’s Z Physiol Chem 75:339

352. Fischer H, Röse H (1912) Über Bilirubinsäure, ein Neues Bilirubin-Abbauprodukt Ber Dtsch Chem Ges 45:1579

353. Fischer H, Röse H (1912) Zur Kenntnis des Gallenfarbstoffs. IV. Mittlg. Hoppe-Seyler’s Z Physiol Chem 82:391

354. Fischer H, Röse H (1912) Über den Abbau des Bilirubins und der Bilirubinsäure. Ber Dtsch Chem Ges 45:3274

355. Fischer H (1913) Bemerkung zu der Publikation W. Küsters “Beiträge zur Kenntniss des Bilirubins und Hämins”. Hoppe-Seyler’s Z Physiol Chem 83:170

356. Fischer H, Röse H (1913) Einwirkung von Natriummethylat auf Bilirubinsäure, Bilirubin, und Hemibilirubin. Ber Dtsch Chem Ges 46:439

357. Fischer H, Röse H (1914) Zur Kenntnis der Gallenfarbstoffe. V. Mittlg. Über die Konstitution der Bilirubinsäure u. des Bilirubins. Hoppe-Seyler’s Z Physiol Chem 89:255

358. Fischer H, Bartholomäus E, Röse H (1913) Zur Kenntniss des Porphyrin Bildung. II. Mittlg. Über Porphyrinogen und seine Beziehungen zum Blutstoff und Dessem Derivativen. Hoppe-Seyler’s Z Physiol Chem 84:262

359. Fischer H (1913) Erwiderung auf die Bemerkungen von O. Piloty im 5. Heft dieser Ber Dtsch Chem Ges 46:1574

360. Küster W (1912) Beiträge zur Kenntniss des Bilirubins und Hämins. Hoppe-Seyler’s Z Physiol Chem 82:463

361. Fischer H, Bartholomäus E (1911) Zur Hämopyrrol-frage. Ber Dtsch Chem Ges 44:3313 362. Fischer H, Bartholomäus E (1912) Einwirkung von Natriumalkoholat auf Pyrrolderivate. I.

Mittlg. Hoppe-Seyler’s Z Physiol Chem 77:185 363. Fischer H, Bartholomäus E (1912) Synthesen des Phyllopyrrols. Ein Beitrag zur

Hämopyrrolfrage. Ber Dtsch Chem Ges 45:466 364. Willstätter R, Asahina Y (1911) Untersuchen Über Chlorophyll: XVII. Reduction von

Chlorophyll I. Liebig’s Ann Chem 385:188 365. Willstätter R, Asahina (1912) Zur Hämopyrrol-Frage. Ber Dtsch Chem Ges 44:3707 366. Fischer H, Bartholomäus E (1912) Die Lösung der Hämopyrrolfrage. Ber Dtsch Chem Ges

45:1979 367. Fischer H, Bartholomäus E (1912) Gewinnung von Phonopyrrolcarbonsäure aus Hämin.

Ber Dtsch Chem Ges 45:1315 368. Fischer H, Bartholomäus E (1912) Synthesen von 2,4-Dimethylpyrrol-5-essigsäure und

2,4-Dimethylpyrrol-5-propionsäure. Ber Dtsch Chem Ges 45:1919 369. Fischer H, Bartholomäus E (1913) Experimentelle Studien Über die Konstitution des Blut-

und Gallenfarbstoffs. Hoppe-Seyler’s Z Physiol Chem 83:50 370. Fischer H, Röse H (1914) Gewinnung der Isophonopyrrolcarbonsäure aus Hämin und eine

Neue Isolierungsmethode der Sauren Spaltprodukte des Hämins und Bilirubins. Ber Dtsch Chem Ges 47:791

References 749

371. Fischer H, Bartholomäus E (1913) Experimentelle Studien Über die Konstitution des Blut- und Gallenfarbstoffs. II. Mittlg. Hoppe-Seyler’s Z Physiol Chem 87:255

372. Fischer H, Röse H (1914) Über die Destillation Einiger Pyrrolcarbonsäuren. Hoppe-Seyler’s Z Physiol Chem 91:184

373. Fischer H (1916) Über Blut- und Gallenfarbstoff. Ergebnisse der Physiologie, biologischen Chemie und Experimentellen Pharmakologie. Rev Phys Biochem Pharm 15:185

374. Fischer H, Orth H (1934) Die Chemie des Pyrrols. Bd. I, Akademische Verlags-gesellschaft M.B.H., Leipzig, p 278

375. Fischer H, Röse H (1913) Einwirkung von Alkoholaten auf Hämin und seine Derivate. I. Mittlg. Hoppe-Seyler’s Z Physiol Chem 87:38

376. Fischer H (1914) Bemerkung zu der Abhandlung von O. Piloty, W. Krannich und H. Will, Zur Konstitution des Blutfarbstoffs: Dipyrryl-methene. Derivate mit Farbstoff-Struktur. Ber Dtsch Chem Ges 47:3266

377. Fischer H (1914) Zur Kenntnis der Gallenfarbstoffe. VI. Mittlg. Über Mesobilirubin und Mesobilirubinogen. Z Biol 65:163

378. Fischer H (1914) Über Mesobilirubin. Ber Dtsch Chem Ges 47:2330 379. Fischer H, Hahn A (1914) Über Brommesoporphyrin und die Reduktion von Blut- und

Gallenfarbstoff bei Gegenwart von Kolloidalem Palladium. Hoppe-Seyler’s Z Physiol Chem 91:174

380. Küster W (1915) Ueber den Chemismus der Bildung des Gallenfarbstoffs aus der Eisenhaltigen Componente des Blutfarbstoffs. Archiv Pharm 253:457

381. Küster W (1915) Über die Konstitution des Hämins und des Bilirubins. Hoppe-Seyler’s Z Physiol Chem 95:152

382. Küster W (1917) Über das Bilirubinammonium und Über Modifikationen des Bilirubins. Hoppe-Seyler’s Z Physiol Chem 99:86

383. Küster W (1915) Beiträge zur Kentniss der Gallenfarbstoff. VIII. Mitteilung. Über das Bilirubin. Hoppe-Seyler’s Z Physiol Chem 94:136

384. Küster W (1920) Über die Bindung des Eisens in der Prosthetischen Gruppe des Blutfarbstoffs und die Konstitution des Hämins. Ber Dtsch Chem Ges 53:623

385. Fischer H, Beller H (1925) Synthese Eines Tetrapyrryl-äthylens und Einiger Derivate des 2,3-Dimethyl-pyrrols. Liebig’s Ann Chem 444:238

386. Fischer H, Eismayer K (1914) Experimentelle Studien Über die Konstitution des Blut- und Gallen-Farbstoffs. III. Ber Dtsch Chem Ges 47:2019

387. Küster W (1917) Über das Bilirubinammonium und Über Modifikation des Bilirubins. X. Mitteilung zur Kenntnis der Gallenfarbstoffe. Hoppe-Seyler’s Z Physiol Chem 99:86

388. Küster W (1921) Einige Neue Beobachtungen beim Studium des Bilirubins. Angew Chem 34:246

389. Küster W (1922) Beiträge zur Kenntnis der Gallenfarbstoffe. XII. Mitteilung. Über die Einwirkung von Diazomethan auf Bilirubin und Biliverdin, die Oxydation des Bilirubins in Alkalischer Lösung und die Einwirkung von Bromwasserstoff – Eissig auf Bilirubin. Hoppe-Seyler’s Z Physiol Chem 121:94

390. Küster W, Haas R (1924) Über die Aufarbeitung von Rindergallenstein. 14. Mittlg. Über Gallenfarbstoff. Hoppe-Seyler’s Z Physiol Chem 141:279

391. Küster W, Heeß W (1925) Beiträge zur Kenntnis der Prosthetischen Gruppe. Ber Dtsch Chem Ges 58:1022

392. Stern AJ (1973) Hans Fischer (1881-1945) Annals NY Acad Sci 206:752 393. Fischer H, Herrmann M (1922) Einige Beobachtungen Über Pyrrole und Pyrrolaldehyde.

Hoppe-Seyler’s Z Physiol Chem 122:1 394. Fischer H, Loy E (1923) Synthetische Versuche Über die Konstitution des Gallenfarbstoffs.

I. Mittlg. Hoppe-Seyler’s Z Physiol Chem 128:59 395. Fischer H, Niemann G (1923) Zur Kenntnis des Gallenfarbstoffs. 7. Mittlg. Hoppe-Seyler’s

Z Physiol Chem 127:317 396. Falk H, Müller N (1985) On the Chemistry of Pyrrole Pigments. Magn Reson Chem 23:353

References750

397. Fischer H, Niemann G (1924) Zur Kenntnis des Gallenfarbstoffs. 8. Mittlg. Mesobiliviolin, Mesobiliviolinogen, Mesobilirubinogen mit Aldehyden unter Bildung von Neuen Spaltprodukten Diazofarbstoff des Mesobilirubins. Hoppe-Seyler’s Z Physiol Chem 137:293

398. Fischer H, Postowsky J (1926) Bestimmung des “Aktiven Wasserstoffs” im Hämin und Bilirubin, Einigen ihrer Derivate und in Pyrrolen. Hoppe-Seyler’s Z Physiol Chem 152:300

399. Fischer H, Niemann G (1925) Zur Kenntnis des Gallenfarbstoffs (IX). Kleiner Mitteilungen. Hoppe-Seyler’s Z Physiol Chem 146:196

400. Fischer H, Schubert M (1923) Über Tetrapyrrylethane (I.). Ber Dtsch Chem Ges 56:2379 401. Fischer H (1925) Über Blutfarbstoff und Einige Porphyrine. Angew Chem 38:981 402. Fischer H, Klarer J (1926) Synthese des Ätioporphyrins, Ätiohemins, und Ätiophyllins.

Liebig’s Ann Chem 448:178 403. Fischer H, Halbig P (1926) Synthese des Iso-Ätioporphyrins, Seines „Hämins” und

„Phyllins”. Liebig’s Ann Chem 448:193 404. Fischer H, Scheyer H (1924) Einwirkung von Halogen auf Substituierte Pyrrole; ein

Dipyrryläthan und Synthese Eines Farbstoffes aus Vier Pyrrolkernen. Liebig’s Ann Chem 439:185

405. Fischer H, Heyse M (1924) Über Tripyrrylmethane. Liebig’s Ann Chem 439:246 406. Fischer H, Amman H (1923) Einige Umsetzungen des 2,4-Dimethyl-3-acetyl-pyrrols und

Über Tripyrryl-methane (I). Ber Dtsch Chem Ges 56:2319 407. Fischer H, Pützer B (1926) Kenntnis der natürlichen Porphyrine. XIX. Mitteilung.

Überführung von Hämin in Protoporphyrin und Eine Neue Darstellung der Mesoporphyrins. Hoppe-Seyler’s Z Physiol Chem 154:39

408. Fischer H, Lindner F (1926) Überführung von Gallenfarbstoff und Bilirubinsäure in Mesoporphyrin. Gewinnung von Hämopyrrol aus Mesobilirubinogen. Hoppe-Seyler’s Z Physiol Chem 161:1

409. Fischer H, Andersag H (1926) Synthese des Kopro- und Iso-Koproporphyrins. Liebig’s Ann Chem 450:201

410. Fischer H, Halbig P, Walach B (1927) Über eine neue Porphyrinsynthese, Oxydation von Porphyrinen und Einige Kleinere Beobachtungen. Liebig’s Ann Chem 452:268

411. Schlack P (1960) William Küster. Lecture at the Uni-Stuttgart 412. Küster W (1927) Über den Chemismus der Porphyrinbildung und die Konstitution des

Hämins. (Eine Entgegnung zu Bemerkungen von H. Fischer.) Hoppe-Seyler’s Z Physiol Chem 163:267

413. Küster H, Kimmich K (1927) Über den Blutfarbstoff. Hoppe-Seyler’s Z Physiol Chem 172:199

414. Papendieck A (1923) Über das Porphyrin der Menschlichen Fäzes. Hoppe-Seyler’s Z Physiol Chem 128:109

415. Papendieck A (1924) Über das Porphyrin der Menschlichen Fäzes. (II Mitteilung) Hoppe-Seyler’s Z Physiol Chem 133:97

416. Fischer H, Schneller K (1924) Zur Kenntnis der Natürlichen Porphyrine. VI. Mitteilung. Über die Verbreitung der Porphyrine in Organen. Nachweis Eines Porphyrins in des Hefe. Hoppe-Seyler’s Z Physiol Chem 135:253

417. Schumm O (1924) Spektroskopisch-chemische Reaktionen Einiger Porphyrine und Ihrer Methylester. Hoppe-Seyler’s Z Physiol Chem 136:243

418. Fischer H (1924) Bemerkungen zu den Abhandlungen von Schumm und Papendieck in Dieser Zeitung Bd. 136, Heft 5 und 6. Hoppe-Seyler’s Z Physiol Chem 138:307

419. Fischer H (1926) Bemerkung zu den Richtigstellungen Schumms. Hoppe-Seyler’s Z Physiol Chem 155:96

420. Schumm O (1926) Spektrochemische Untersuchungen an Porphyrinen und Hämatinen. (Fortsetzung.) I. Über den Nachweis von Koproporphyrin und die Bedeutung Spektrochemischer Methoden für die Porphyrin- und Porphyratinforschung. II. Über das im Blutserum Kranker Auftretende Hämatin. Hoppe-Seyler’s Z Physiol Chem 152:1

References 751

421. Schumm O (1926) Weitere Beiträge zur Kenntnis der Natürlichen Porphyrine und der Porphyrinatine. Hoppe-Seyler’s Z Physiol Chem 153:225

422. Schumm O (1926) Richtigstellung zur Abhandlung von Hans Fischer und Hans Hilmer: “Koproporphyrin-Synthese durch Hefe und Ihre Beeinflussung” und der “Bemerkung” von Hans Fischer. Hoppe-Seyler’s Z Physiol Chem 156:159

423. Fischer H, Hilmer H (1926) Über Koproporphyrin-Synthese durch Hefe und Ihre Beeinflussung. IV. Mitteilung. Hoppe-Seyler’s Z Physiol Chem 153:167

424. Schumm O (1928) Bemerkung zu dem Vortrag von Hans Fischer: “Über Porphyrine und Ihre Synthese”. Ber Dtsch Chem Ges 161:784

425. Fischer H, Zeile K (1929) Synthese des Hämatoporphyrins, Protoporphyrins, und Hämins. Liebig’s Ann Chem 468:98

426. Fischer H (1927) Über Porphyrine und Ihre Synthesen. Ber Dtsch Chem Ges 60:2611 427. Fischer H (1928) Bemerkung zu Meinen vor der Deutschen Chemischen Gesellschaft

Gehalten Vortrag. Ber Dtsch Chem Ges 61:1596 428. Olah GA, Prakash GKS, Saunders M (1983) Conclusion of the Classical-nonclassical Ion

Controversy Based on the Structural Study of the 2-Norbornyl Cation. Acc Chem Res 16:440

429. Fischer H, Treibs A (1927) Über Ätioxantho- und Mesoxantho-porphyrinogen. Liebig’s Ann Chem 457:209

430. Fischer H, Andersag H (1927) Synthese des b-Iso-Koproporphyrins und der Opsopyrrolcarbonsäure. Liebig’s Ann Chem 458:117

431. Fischer H, Stangler G (1927) Synthese des Meosporphyrins, Mesohämins und Über die Konstitution des Hämins. Liebig’s Ann Chem 459:53

432. Pfeiffer P (1929) William Küster, 1863-1929. Angew Chem 42:785 433. Lemberg R, Legge JW (1949) Hematin Compounds and Bile Pigments. Interscience

Publishers, New York and London 434. Willstätter R (1949) Aus Meinen Leben. Verlag Chemie, GmbH, Weinheim, p 184 435. Willstätter R (1965) From My Life. Hornig LS (transl). WA Benjamin, Inc, New York, p 194 436. Fischer H (1930) Hämin, Bilirubin und Porphyrine. Naturwissenschaften 18:1026 437. Watson CJ (1965) Reminiscences of Hans Fischer and His Laboratory. Perspect Biol Med

8:419 438. Fischer H, Hess R (1931) Über Neo-, Xantho-neobilirubinsäure und Partialsynthese des

Mesobilirubins und Mesobilirubinogens (Urobilinogens). Hoppe-Seyler’s Z Physiol Chem 194:193

439. Schumm O (1928) Über Einige Neue Verfahren zur Gewinnung von Häminderivaten. Hoppe-Seyler’s Z Physiol Chem 176:122

440. Schumm O (1928) Über die Gewinnung von Häminderivaten durch Brenzreaktionen. 2. Mitteilung. I. Darstellung des Pyratins aus Hämins durch die Resorcinschmelze. II. Eisenung und Eigenschaften des Pyroporphyrins. III. Eisenung von Porphyrinen in der „Eisen-Phenolschmelze” und Umwandlung von Eisenporphyratinen durch Phenole und Phenolschwefelsäure. Hoppe-Seyler’s Z Physiol Chem 178:1

441. Bonnett R, McDonagh AF (1970) Oxidative Cleavage of the Haem System: The Four Isomeric Biliverdins of the IX Series. J Chem Soc Chem Commun:238

442. Fischer H, Adler E (1931) Synthese des Bilirubin- und Xanthobilirubinsäure und Ihre Isomeren, sowie Synthese von Tripyrranen und Bilirubinoiden Farbstoffen. Hoppe-Seyler’s Z Physiol Chem 197:237

443. Siedel W, Fischer H (1933) Über die Konstitution des Bilirubins, Synthesen der Neo- und der Iso-neoxanthobilirubinsäure. Hoppe-Seyler’s Z Physiol Chem 214:145

444. Fischer H, Adler (1931) Synthese des Mesobilirubinogens und der Neobilirubinsäure, eines Mesobilirubins und einer Neoxanthobilirubinsäure sowie von (1,8)-Dioxy-tripyrro-di-enen. Hoppe-Seyler’s Z Physiol Chem 200:209

445. Ma, J-S, Chen Q-Q, Wang C-Q, Liu Y-Y, Yan F, Cheng L-J, Jin S, Falk H (1995) A Novel 16,24-Dehydrobiladiene-ab System; The Reaction of Xanthobilirubic Acid Methyl Ester with Bromine. Monatsh Chem 126:201

References752

446. Chen Q-Q, Ma, J-S, Wang C-Q, Liu Y-Y, Yan F, Cheng L-J, Jin S, Falk H (1995) 2-bis-Dipyrrinone-9-yl-ethene – a Novel b-homo-Verdin Chromophore: the Reaction of 9-Methyl-10H-dipyrrinones with Bromine. Monatsh Chem 126:983

447. Fischer H, Neumann FW (1932) The Chemistry of Animal Pigments. Ann Rev Biochem 1:527

448. Fischer H, Fröwis W (1931) Synthese von Oxypyrromethenen und Über Einige Derivate des Koproporphyrins I. Hoppe-Seyler’s Z Physiol Chem 195:49

449. Fischer H, Orth H (1934) The Structural Chemistry of the Animal Pigments. Ann Rev Biochem 3:410

450. Lemberg R, Barcroft J (1932) Uteroverdin, the Green Pigment of the Dog Placenta. Proc Roy Soc London 110B:362

451. Lemberg R (1932) Über Dehyro-bilirubin. Liebig’s Ann Chem 499:25 452. Fischer H, Hartmann P (1934) Synthese des Oxyhämopyrrols, der Iso-neo-, der Iso-

xanthobilirubinsäure und Über den Kryptopyrroläther. Hoppe-Seyler’s Z Physiol Chem 226:116

453. Grunewald JO, Cullen R, Bredfeldt J, Strope ER (1975) An Efficient Route to Xanthobilirubic Acid, an Oxodipyrrylmethene. Org Prep Proc Int 7:103

454. Siedel W (1935) Neue Synthesen der Neo- und Iso-neoxanthobilirubinsäure. Vorarbeiten zur Synthese Natürlicher Bilirubinoide. Hoppe-Seyler’s Z Physiol Chem 231:167

455. Fischer H, Haberland H (1935) Über die Konstitution des Bilirubins Sowie die Seiner Azofarbstoffe und die Gmelinsche Reaktion. Hoppe-Seyler’s Z Physiol Chem 232:236

456. Siedel W (1937) Synthese des Mesobilirubins (= Mesobilirubin-IX, a). Hoppe-Seyler’s Z Physiol Chem 245:257

457. Siedel W (1935) Synthese des Glaukobilins, Sowie Über Urobilin und Mesobiliviolin. Hoppe-Seyler’s Z Physiol Chem 237:8

458. Fischer H, Reinecke H (1939) Synthese Zweier Vinyl-substitutierter Bilirubinoide. Hoppe-Seyler’s Z Physiol Chem 258:9

459. Bonnett R, McDonagh AF (1969) Methylvinylmaleimide (the ‘Nitrite Body’) from Chromic Acid Oxidation of Tetrapyrrole Pigments. Chem & Ind (London):107

460. Lemberg R (1935) CLXI. Transformation of Haemins into Bile Pigments. Biochem J 29:1322

461. Lightner DA, Quistad GB (1972) Methylvinylmaleimide from Bilirubin Photooxidation. Science 175:324

462. Fischer H, Plieninger H (1942) Synthese des Biliverdins (Uteroverdins) und Bilirubins. Naturwissenschaften 30:382

463. Pleininger H, Lichtenwald H (1942) Über Eine Neue Darstellung von Oxypyrromethenes Durch Alkalische Kondensation von Oxypyrrolen mit Pyrrol-a-aldehyden, Sowie Über Weitere Versuche zur Synthese von acetylsubstituierten Gallenfarbstoffen und Über Tripyrrene. Hoppe-Seyler’s Z Physiol Chem 273:206

464. Fischer H, Reinecke H (1939) Über Tripyrrene. Hoppe-Seyler’s Z Physiol Chem 259:86 465. Fischer H, Treibs A (1926) Über Abbau des Blutfarbstoffs und Wiederaufbau von

Porphyrinen aus Opsopyrrol und Opsopyrrolcarbonsäure. Liebig’s Ann Chem 450:132 466. Fischer H, Reinecke H, Lichtenwald H (1939) Über Oxy-amino-pyrromethene, ein Beitrag

zur Kenntnis der Pentdyopent-Reaktion. Hoppe-Seyler’s Z Physiol Chem 257:190 467. Jellinek K, Jellinek E (1919) Chemische Zersetzung und Electrolytische Bildung von

Natriumhydrosulfit. Z Naturforsch 93:325 468. Lisler MW, Garvie RC (1959) Sodium Dithionite, Decomposition in Aqueous Solution and

in the Solid State. Can J Chem 37:1567 469. Stoll MS, Gray CH (1977) The Preparation and Characterization of Bile Pigments.

Biochem J 163:59 470. Blanckaert N, Heirwegh KPM, Compernolle F (1976) Synthesis and Separation by Thin

Layer Chromatography of Bilirubin-IX Isomers. Biochem J 155:405 471. Kufer W, Scheer H (1979) Chemical Modification of Biliprotein Chromophores. Z

Naturforsch C: J Biosci 34:776

References 753

472. Kufer W, Scheer H (1982) Rubins and Rubinoid Addition Products from Phycocyanin. Z Naturforsch C: J Biosci 37C:179

473. McDonagh AF (1975) Thermal and Photochemical Reactions of Bilirubin. Ann NY Acad Sci 244:553

474. McDonagh AF, Assisi F (1972) The Ready Isomerization of Bilirubin-IX-a in Aqueous Solution. Biochem J 129:797

475. McDonagh AF, Assisi F (1972) Direct Evidence for the Acid-catalyzed Isomeric Scrambling of Bilirubin IX-a. J Chem Soc Chem Commun 117

476. McDonagh AF, Assisi F (1971) Commercial Bilirubin: A Trinity of Isomers. FEBS Lett 18: 315

477. Ammon U (2004) German as an International Language of the Sciences – Recent Past and Present. In: Gardt A, Hüppauf B (eds) Globalization and the Future of German. Mouton de Gruyter, Berlin

478. Sanders RH (2010) German. Biography of a Language. Oxford University Press, New York 479. Gross PLK, Gross EM (1927) College Libraries and Chemical Education. Science 66:385 480. Fieser LF, Fieser M (1959) Steroids. Reinhold Publishing Corp, Waverly Press, Inc,

Baltimore 481. Keana JFW, Johnson WS (1964) Racemic Cholesterol. Steroids 4:457 482. Pimentel GC, McClellan AL (1960) The Hydrogen Bond. WH Freeman and Co, San

Francisco and London 483. Lemberg R (1932) Über Dehydro-bilirubin. Liebig’s Ann Chem 499:25 484. Fowweather FS (1932) Bilirubin and the van den Bergh Reaction. Biochem J 26:165 485. Gray CH (1953) The Bile Pigments. Methuen, London 486. Gray CH, Nicholson DC, Nicolaus RA (1958) The IX-a Structure of the Common Bile

Pigments. Nature 187:183 487. Plieninger H, Decker M (1956) Eine neue Synthese für Pyrrolone, insbesondere für

“Isooxyopsopyrrol” und “Isooxypyrrolecarbonsäure”. Liebig’s Ann Chem 598:198 488. Grob CA, Ankli P (1954) Die Tautomerie der a-Amino and a-Oxypyrrole. Untersuchungen

in der Pyrrolreihe. 6. Mitteilung. Helv Chim Acta 37:1256 489. Grob CA, Ankli P (1949) Über a-Pyrrolone. 2. Mitteilung. Helv Chim Acta 32:2010 490. Gray CH, Nicholson DC (1957) Structure of Stercobilin. Nature 179:264 491. Gray CH, Nicholson D (1957) Structure of d-Urobilin. Nature 180:336 492. Watson CJ, Weimer M, Hawkinson V (1960) Differences in the Formation of Mesobiliviolin

and Glaucobilin from d- and i-Urobilins. J Biol Chem 235:787 493. Gray CH, Kulczycka A, Nicholson DC (1961) Prototropy of Bilirubin to a Verdinoid

Pigment. J Chem Soc:2268 494. Gray CH (1961) Bile Pigments in Health and Disease. Thomas, Springfield, Illinois 495. Fog J, Jellum E (1963) Structure of Bilirubin. Nature 198:88 496. Fog J, Bugge-Asperheim B (1964) Stability of Bilirubin. Nature 203:756 497. von Dobeneck H, Brunner E (1965) Über Eine Ordnung der Dipyrromethene und Über die

Betainstruktur des Bilirubins. Hoppe-Seyler’s Z Phys Chem 341:157 498. ÓhEocha C (1965) Phycobilins. In: Goodwin TW (ed) Chemistry and Biochemistry of

Plant Pigments. Academic Press, New York 499. Brodersen R, Flodgaard H, Krogh-Hansen J (1967) Intramolecular Hydrogen Bonding in

Bilirubin. Acta Chem Scand 21:2284 500. Bouchier IAD, Billing BH (eds) (1967) Bilirubin Metabolism. Blackwell Scientific

Publications, Oxford and Edinburgh 501. With TK (1968) Bile Pigments. Chemical, Biological and Clinical Aspects. Kennedy JP

(trans). Academic Press, New York 502. Ostrow JD (1972) Mechanisms of Bilirubin Photodegradation. Semin Hematol 9:113 503. Ostrow JD (1972) Photochemical and Biochemical Basis of the Treatment of Neonatal

Jaundice. In: Popper H, Schaffner F (eds) Progress in Liver Disease, vol IV. Grune & Stratton, Inc, New York, p 447

References754

504. Nichol AW, Morell DB (1969) Tautomerism and Hydrogen Bonding in Bilirubin and Biliverdin. Biochim Biophys Acta 177:599

505. Kuenzle CC (1970) Bilirubin Conjugates of Human Bile. Nuclear-magnetic-resonance, Infrared and Optical Spectra of Model Components. Biochem J 119:395

506. Hutchinson DW, Johnson B, Knell AJ (1971) Tautomerism and Hydrogen Bonding in Bilirubin. Biochem J 123:483

507. Odell GB, Schaffer R, Simopoulos AP (eds) (1974) Phototherapy in the Newborn: An Overview. US National Academy of Sciences, Washington, DC

508. Bakken AF, Fog J (eds) (1975) Metabolism and Chemistry of Bilirubin and Related Tetrapyrroles. Pediatric Research Institute, Rikshospitalet, Oslo, Norway. Proceedings of the Bilirubin Meeting in Hemsedal, Norway, September 1974

509. Berk PD, Berlin NI (eds) (1977) Chemistry and Physiology of Bile Pigments. DHEW Publ No (NIH) 77-1001, US Dept of Health, Education and Welfare, National Institutes of Health, Bethesda, Maryland

510. Bonnett R, Davies JE, Hursthouse MB (1976) Structure of Bilirubin. Nature 262:326 511. Bonnett R, Davies JE, Hursthouse MB, Sheldrick GM (1978) The Structure of Bilirubin.

Proc Royal Soc London B202:249 512. Sheldrick WS, Becker W (1979) Crystal and Molecular Structure of Diethoxybilirubin

Diethyl Ester. Z Naturforsch 34b:1542 513. Kratky C, Jorde C, Falk H, Thirring K (1983) Crystal Structure of the Mono-lactim Ether

of a Bilatriene-abc Derivative at 101 K. Tetrahedron 39:1859 514. Becker W. Sheldrick WS (1978) Bile Pigment Structures. II. The Crystal Structure of

Mesobilirubin-IXa-bis(chloroform). Acta Cryst B34:1298 515. LeBas G, Allegret A, DeRango C (1977) Conformation and Relations with Optical

Rotation Properties of Bilirubin Molecule. Proceedings of the Fourth European Crystallographic Meeting, Aug 30-Sept 3, Abst PI107:310

516. LeBas G, Allegret A, Mauguen Y, DeRango C, Bailly M (1980) The Structure of Triclinic Bilirubin Chloroform-methanol Solvate. Acta Cryst B36:3007

517. Mugnoli A, Manitto P, Monti D (1978) Structure of Di-isopropylammonium Bilirubinate. Nature 273:568

518. Mugnoli A, Manitto P, Monti D (1983) Structure of Bilirubin-IXa (Isopropylammonium Salt) Chloroform Solvate, C33H34N4O6

2-·2C3H10N+·2CHCl3. Acta Cryst C39:1287 519. Sheldrick WS (1976) Crystal and Molecular Structure of Biliverdin Dimethyl Ester. J Am

Chem Soc Perkin Trans II:1457 520. Cullen DL, Black PS, Meyer Jr EF, Lightner DA, Quistad GB (1977) The Crystal and

Molecular Structure of an Oxodipyrromethene Related to Bilirubin. Tetrahedron 33:477 521. Cullen DL, Pèpe G, Meyer Jr EF, Falk H, Grubmayr K (1979) syn and anti-Conformation

in Oxo-dipyrromethenes: Crystal and Molecular Structure of 3,4-Dimethyl-2,2¢-pyrromethen-5(1H)-one and its N-Methyl Derivative. J Chem Soc Perkin Trans II:999

522. Hori A, Mangani S, Pèpe G, Meyer Jr EF (1981) Crystal and Molecular Structure of a Photoisomer of an Oxo-dipyrromethene. The E-isomer of 3,4-Dimethyl-2,2¢-pyrrometh-5(1H)-one. J Chem Soc Perkin Trans II:1525

523. Gossauer A, Blacha M, Sheldrick WS (1976) Synthesis and X-ray Crystal Structure of Two Stereoisomeric Derivatives of 3,4-Dihydropyrromethen-5(1H)-one. J Chem Soc Chem Commun:764

524. Sheldrick WS, Borkenstein A, Blacha-Puller M, Gossauer A (1977) Stereoisomerism in Partial Bile Pigment Structures. The Crystal Structures of Z and E Isomers of 5¢-Ethoxycarbonyl-3,4-dihydro-3¢,4¢-dimethyl-5(1H)-2,2¢-pyrromethenone and Their Reaction Products with Et3O+BF4

-. Acta Cryst B33: 3625 525. Falk H, Gergely S, Grubmayr K, Hofer O (1977) Die Lactam-Lactim Tautomerie von

Gallenpigmenten. Liebig’s Ann Chem 1977:565 526. Falk H, Grubmayr K, Thirring K, Gurker H (1978) Beiträge zur Chemie der Pyrrolpigmente,

21. Mitt. Röntgenphotoelektronenspektrometrische Untersuchungen des N1s-Niveaus von Gallenpigmenten. Monatsh Chem 109: 1183

References 755

527. Falk H, Hofer O, Lehner H (1974) Beiträge zur Chemie der Pyrrolpigmente, 2. Mitt. Röntgenphotoelektronenspektren Einiger Pyrrolpigmente. Monatsh Chem 105:366

528. Falk H, Hofer O (1974) Beiträge zur Chemie der Pyrrolpigmente, 4. Mitt. Die N-H Tautomerie von Substituierten Pyrromethenen: Zur Dynamik der Protonentransfers aus der Sicht Eines Quantenchemischen Verfahrens (CNDO/2). Monatsh Chem 105:995

529. Severini-Ricca GS, Manitto P, Monti D (1974) The Carbon-13 Nuclear Magnetic Resonance Spectra of Bilirubin and its Derivatives. A Confirmation of the bis-Lactam Form for these Biladiens (1974). In: Bakken AF, Fog J (eds) Proceedings of a Conference on the Metabolism and Chemistry of Bilirubin and Related Tetrapyrroles. Pediatric Research Institute Rikshospitalet, Oslo, Norway

530. Severini-Ricca G, Manitto P, Monti D, Randall EW (1975) The Carbon-13 Nuclear Magnetic Resonance Spectra of Bilirubin and its Derivatives. Gazz Chim Ital 105:1273

531. Jakobsen JH, Bildsøe H, Dønstrup S, Sorensen OW (1984) Simple One-dimensional NMR Experiments for Heteronuclear Chemical-shift Correlation. J Magn Reson 57:324

532. Hansen PE, Jakobsen JH (1984) A Natural Isotopic Abundance Nitrogen-15 Investigation of Bilirubin IX-a. Org Magn Reson 22:688

533. Falk H, Müller N (1985) On the Chemistry of Pyrrole Pigments 60 – Natural Isotopic Abundance 15N NMR Spectra of Verdinoid Bile Pigments and Their Partial Structures. Magn Reson Chem 23:353

534. Blackwood JE, Gladys CL, Loening KL, Petrarca AE, Rush JE (1968) Unambiguous Specification of Stereoisomerism About a Double Bond. J Am Chem Soc 90:509

535. Rimington C, Gray CH (1976) Max Rudolf Lemberg, 1896-1976. Biographical Memoirs of Fellows of the Royal Society 22:255

536. ÓhEocha C (1968) The Formation of Bile Pigments. In: Goodwin TW (ed) Porphyrins and Related Compounds. Academic Press, New York, p 91

537. Kuenzle CC, Weibel MH, Pelloni RR (1973) The Reaction of Bilirubin with Diazomethane. Biochem J 133:357

538. Hutchinson, DW, Johnson B, Knell AJ (1973) The Synthesis of Esters of Bilirubin. Biochem J 133:493

539. Burke MJ, Pratt DC, Moscowitz A (1972) Low-temperature Absorption and Circular Dichroism Studies of Phytochrome. Biochemistry 11:4025

540. Falk H, Grubmayr K, Herzig U, Hofer O (1974) The Configurations of the Isomeric 3,4-Dimethyl-5-(1H)-2,2¢-pyrromethenones. Tetrahedron Lett:559

541. Overhauser A (1913) Polarization of Nuclei in Metals. Phys Rev 92:411 542. Neuhaus D, Williamson MP (2000) The Nuclear Overhauser Effect in Structural and

Conformational Analysis, 2nd ed. John Wiley & Sons, Inc, New York 543. Huggins MT, Billimona F (2007) Nuclear Overhauser Effect Spectroscopy. J Chem Educ

84:471 544. Kaplan D, Navon G (1981) Nuclear Magnetic Resonance Studies of the Conformation of

Bilirubin and Its Derivatives in Solution. J Chem Soc Perkin Trans II:1374 545. Falk H, Grubmayr K, Haslinger E. Schlederer T, Thirring K (1978) Die Stereoisomeren

(Geometrisch Isomeren) Biliverdindimethylester – Struktur, Konfiguration und Konformation. Monatsh Chem 109:1451

546. Falk H, Grubmayr K, Magauer K, Müller N, Zrunek U (1983) Phytochrome Model Studies: The Tautomerism at N22-N23 of Unsymmetrically Substituted Bilatrienes-abc and 2,3-Dihydrobilatrienes-abc. Isr J Chem 23:187

547. Barañano DE, Rao M, Ferris CD, Snyder SH (2002) Biliverdin Reductase: A Major Physiologic Cytoprotectant. Proc Natl Acad Sci USA 99:16093

548. Joule JA, Mills K (2010) Heterocyclic Chemistry, 5th ed. J Wiley & Sons, Inc, New York, p 635

549. Frankenberg N, Lagarius JG (2003) Phycocyanobilin: Ferredoxin Oxidoreductase of Anabaena sp. PCC7120. J Biol Chem 278:9219

550. McDonagh AF, Lightner DA (2003) Attention to Stereochemistry. Chem Eng News 81:2

References756

551. Ritter SK (2003) Mind Your E’s and Z’s. Chem Eng News 81:29 552. Kuenzle CC, Pelloni RR, Weibel MH (1972) A Proposed Novel Structure for the Metal

Chelates of Bilirubin. Biochem J 130:1147 553. Kuenzle CC, Weibel MH, Pelloni RR, Hemmerich P (1973) Structure and Conformation of

Bilirubin. Opposing Views that Invoke Tautomeric Equilibria, Hydrogen Bonding and a Betaine May Be Reconciled by a Single Resonance Hybrid. Biochem J 133:364

554. Moffitt W, Moscowitz A (1959) Optical Activity in Absorbing Media. J Chem Phys 30:648 555. Moscowitz A (1967) Some Remarks on the Interpretation of Natural and Magnetically

Induced Optical Activity Data. Proc Royal Soc London, Series A, Math Phys Sci 297:16 556. Deutsche CW, Lightner DA, Woody RW, Moscowitz A (1969) Optical Activity. Ann Rev

Phys Chem 20:407 557. Blauer G, King TS (1968) Optical Rotatory Dispersion of Bilirubin Bound to Serum

Albumin. Biochem Biophys Res Commun 31:678 558. Blauer G, King TE (1970) Interactions of Bilirubin with Bovine Serum Albumin in

Aqueous Solution. J Biol Chem 245:372 559. Blauer G, Harmatz D, Naparstek A (1970) Circular Dichroism of Bilirubin Human Serum

Albumin Complexes in Aqueous Solution. FEBS Lett 9:53 560. Blauer G, Harmatz D, Snir J (1972) Optical Properties of Bilirubin-Serum Albumin

Complexes in Aqueous Solution. I. Dependence on pH. Biochim Biophys Acta 278:68 561. Blauer G (1976) Physicochemical Methods in the Study of Bilirubin Binding: Optical

Rotation and Circular Dichroism. In: Bergsma D, Blondheim SH (eds), Bilirubin Metabolism in the Newborn (II), Birth Defects. Original Article Series, vol XII, no. 2:134

562. Blauer G, Harmatz D (1972) Optical Properties of Bilirubin-Serum Albumin Complexes in Aqueous Solution. II. Effects of Electrolytes and of Concentration. Biochim Biophys Acta 278:89

563. Blauer G, Lavie E, Silfen J (1977) Relative Affinities of Bilirubin for Serum Albumins from Different Species. Biochim Biophys Acta 492:64

564. Lavie E, Blauer G (1979) Circular Dichroism and Hydrodynamic Measurements of Ternary Protein – Two Ligand Systems: Serum Albumin-Bilirubin-Drug or Alcohol. Arch Biochem Biophys 193:191

565. Blauer G (1986) Complexes of Bilirubin with Proteins. Biochem Biophys Acta 884:602 566. Lightner DA, Gurst JE (2000) Organic Conformation Analysis and Stereochemistry from

Circular Dichroism Spectroscopy. Wiley-VCH, New York 567. Djerassi C (1960) Optical Rotatory Dispersion. McGraw-Hill, New York 568. Newman MS, Darlak RS, Tsai L (1967) Optical Properties of Hexahelicene. J Am Chem

Soc 89:6191 569. Lightner DA, Hefelfinger DT, Frank GW, Powers TW, Trueblood KN (1971) The Absolute

Configuration of Hexahelicene. Nature Phys Sci 232:124 570. Lightner DA, Hefelfinger DT, Frank GW, Powers TW, Trueblood KN (1972) Hexahelicene.

The Absolute Configuration. J Am Chem Soc 94:3492 571. Moscowitz A, Krueger WC, Kay IT, Skewes G, Bruckenstein S (1964) On the Origin of the

Optical Activity in the Urobilins. Proc Natl Acad Sci USA 52:1190 572. Manitto P, Severini-Ricca GS, Monti D (1974) The Conformation of Bilirubin and Its

Esters. Gazz Chim Ital 104:633 573. Knell AJ, Hutchinson DW, Johnson B (1972) Intramolecular Hydrogen Bonds in Bilirubin.

Abstracts of the 7th Annual Meeting of the European Association for the Study of the Liver (Arnhem, The Netherlands, 7-9 September 1972), Digestion 6:288

574. Knell AJ, Hancock F, Hutchinson DW (1975) Bilirubin Revisted. In: Bakken AF, Fog J (eds) Proceedings of a Conference on the Metabolism and Chemistry of Bilirubin and related Tetrapyrroles. Pediatric Research Institute Rikshospitalet, Oslo, Norway, p 234

575. Navon G (1976) The Nuclear Magnetic Resonance Spectrum of Bilirubin. In: Bergsma D, Blondheim SH (eds) Bilirubin Metabolism in the Newborn (II) – Birth Defects: Original Article Series, vol XII, no 2, Elsevier, New York

References 757

576. Kaplan D, Panigel R, Navon G (1977) Carbon-13 NMR Spectrum of Bilirubin. Spectros Lett 10:881

577. Kaplan D, Navon G (1981) Carbon-13 Nuclear Magnetic Resonance Study of the Motional Behaviour of Bilirubin and of Some of Its Derivatives. Org Magn Reson 17:79

578. Kaplan D, Navon G (1981) Nuclear Magnetic Resonance Studies of the Conformation of Bilirubin and Its Derivatives in Solution. J Chem Soc Perkin Trans II:1374

579. Kaplan D, Navon G (1982) Studies of the Conformation of Bilirubin and Its Dimethyl Ester in Dimethyl Sulphoxide Solutions by Nuclear Magnetic Resonance. Biochem J 201:605

580. Kaplan D, Navon G (1983) NMR Spectroscopy of Bilirubin and Its Derivatives. Isr J Chem 23:177

581. Nogales D, Lightner DA (1995) On the Structure of Bilirubin in Solution. J Biol Chem 270:73

582. Dörner T, Knipp B, Lightner DA (1997) Heteronuclear NOE Analysis of Bilirubin Solution Conformation and Intramolecular Hydrogen Bonding. Tetrahedron 53:2697

583. Rohmer T, Matysik J, Mark F (2011) Solvation and Crystal Effects Studied by NMR Spectroscopy and Density Functional Theory. J Phys Chem A 115:11696

584. Metzroth T, Lenhart M, Gauss J (2008) A Quantum Mechanical Investigation of the Geometry and NMR Chemical Shifts of Bilirubin. Appl Magn Reson 33:457

585. Brown SP, Zhu XX, Saalwächter K, Spiess HW (2001) An Investigation of the Hydrogen-bonding Structure in Bilirubin by 1H Double-quantum Magic-angle Spinning Solid-state NMR Spectroscopy. J Amer Chem Soc 123:4275

586. Scholtan N, Gloxhuber C (1966) Die Eiweißbindung von Bilirubin und Bromsulfalein. Arzneim-Forsch (Drug Research) 16:520

587. Schellman JA (1968) Symmetry Rules for Optical Rotation. Acc Chem Res 1:144 588. Lightner DA (1979) Derivatives of Bile Pigments. In: Dolphin D (ed) The Porphyrins, vol

VI. Academic Press, Inc, Chap 8 589. Fischer H, Halbach H, Stern A (1935) Über Stercobilin und Seine Optische Aktivität.

Liebig’s Ann Chem 519:254 590. Schwartz S, Watson CJ (1942) Isolation of a Dextrorotatory Urobilin from Human Fistula

Bile. Proc Soc Exper Biol Med 49:641 591. Gray CH, Jones PM, Klyne W, Nicholson DC (1959) Optical Activity of Stercobilin and

d-Urobilin. Nature 184:41 592. Woolley PV III, Hunter MJ (1970) Binding and Circular Dichroism Data on Bilirubin-

Albumin 0in the Presence of Oleate and Salicylate. Arch Biochem Biophys 148:197 593. Blauer G, Lavie E (1975) The Interaction of Low-molecular Weight Compounds with

Serum Albumin as Measured by Optical Methods. Circular Dichroism of Bilirubin-human Serum Albumin Complexes in the Presence of Alcohols in Aqueous Solution. Protein-Ligand Interactions. Walter de Gruyter & Co, Berlin

594. Harada N, Nakanishi K (1983) Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry. University Science Books, Mill Valley, California

595. Hansen AaE (2005) Molecular Exciton Approach to Anisotropic Absorption and Circular Dichroism. I. General Formulation. Monatsh Chem 136:253

596. Hansen AaE (2005) Molecular Exciton Approach to Anisotropic Absorption and Circular Dichroism. II. The Partial Optic Axis and Its Application in Molecular Exciton Theory. Monatsh Chem 136:275

597. Blauer G (1983) Optical Activity of Bile Pigments. Isr J Chem 23:201 598. Blauer G, Wagnière G (1975) Conformation of Bilirubin and Biliverdin in Their Complexes

with Serum Albumin. J Am Chem Soc 97:1949 599. Manitto P, Monti D (1976) Free-energy Barrier of Conformational Inversion in Bilirubin. J

Chem Soc Chem Commun:122 600. Manitto P, Monti D (1973) Acid-catalyzed Addition of Alcohols and Thiols to Bilirubin.

Experientia 29:137 601. Navon G, Frank S, Kaplan D (1984) A Nuclear Magnetic Resonance Study of the

Conformation and Interconversion Between the Enantiomeric Conformers of Bilirubin and Mesobilirubin in Solution. J Chem Soc Perkin Trans II:1145

References758

602. Falk H, Hofer O (1974) Beiträge zur Chemie der Pyrrolpigmente, 4. Mitt. Die N-H-Tautomerie von Substitutieren Pyrromethenen: Zur Dynamik des Protontransfers aus der Sicht Eines Quantenchemischen Verfahrens (CNDO/2). Monatsh Chem 105:995

603. Favini G, Pitea D, Manitto P (1979) Conformational Studies on Bilirubin. I. Intramolecular Energy Map for 3,3¢-Dimethyl-dipyrrol-2-ylmethane. Nouveau J Chim 3:299

604. Falk H, Höllbacher G, Hofer O (1979) Konformationsanalyse von Gallenfarbstoffen mit Hilfe von Kraftfeldrechnungen. Monatsh Chem 110:1025

605. Falk H, Höllbacher G, Hofer O (1981) Beiträge zur Chemie der Pyrrolpigmente, 39. Mitt. Ein Kraftfeldmodell zur Konformationsanalytischen Untersuchung von Gallenfarbstoffen. Monatsh Chem 112:391

606. Falk H, Müller N (1981) Beiträge zur Chemie der Pyrrolpigmente, 41. Mitt. Kraftfeldrechnungen an Gallenfarbstoffen: Die Energiehyperfläche Verdinoider Pigmente. Monatsh Chem 112:791

607. Falk H, Müller N (1981) Beiträge zur Chemie der Pyrrolpigmente, 42. Mitt. Kraftfeldrechnung an Gallenfarbstoffen: Die Energiehyperfläche Rubinoide Pigmente. Monatsh Chem 112:1325

608. Falk H, Müller N (1983) Forcefield Calculations on Linear Polypyrrole Systems. Tetrahedron 39:1875

609. Lightner DA, Person RV, Peterson BR, Puzicha G, Pu Y-M, Boiadjiev SE (1991) Conformational Analysis and Circular Dichroism of Bilirubin, the Yellow Pigment of Jaundice. Biomolec Spectrosc II, SPIE 1432:2

610. Person RV, Boiadjiev SE, Peterson BR, Puzicha G, Lightner DA (1991) Circular Dichroism from Exciton Coupling. Conformation Analysis of Bilirubin, the Neurotoxic Yellow Pigment of Jaundice. 4th International Conference on Circular Dichroism Spectroscopy, Bochum, FRG, 9-13 September, p 55

611. Shelver WL, Rosenberg H, Shelver WH (1992) Molecular Conformation of Bilirubin from Semiempirical Molecular Orbital Calculations. Int J Quantum Chem 441:141

612. Barnes JC, Paton JD, Damewood JR Jr, Mislow K (1981) Crystal and Molecular Structure of Diphenylmethane. J Org Chem 46:4975

613. Gust D, Mislow K (1973) Analysis of Isomerization in Compounds Displaying Restricted Rotation of Aryl Groups. J Am Chem Soc 95:1535

614. Falk H, Grubmayr K. Höllbacher G, Hofer O, Leodolter A, Neufingerl E, Ribó JM (1977) Beiträge zur Chemie der Pyrrolpigmente, 18. Mitt. Pyrromethenone – Partialstrukturen von Gallenpigmenten: Struktur und Eigenschaften in Lösung. Monatsh Chem 108:1113

615. Falk H, Vormayr G, Margulies L, Metz S, Mazur Y (1986) A Linear Dichroism Study of Pyrromethene, Pyrrometheneone- and Bilatriene-abc Derivatives. Monatsh Chem 117:849

616. Trull FR, Ma JS, Landen GL, Lightner DA (1983) Hydrogen Bonding of Bilirubin and Pyrromethenones in Solution. Isr J Chem 23:211

617. Nogales DF, Ma J-S, Lightner DA (1993) Self-association of Dipyrrinones Observed by 2D-NOE NMR and Dimerization Constants Calculated from 1H-NMR Chemical Shifts. Tetrahedron 49:2361

618. Person RV (1993) Conformational Analysis of Bilirubin and Its Analogues. Ph.D. Dissertation, University of Nevada, Reno

619. Person RV, Peterson BR, Lightner DA (1994) Bilirubin Conformational Analysis and Circular Dichroism. J Am Chem Soc 116:42

620. Müller N, Falk A (1992) “Ball and Stick” Computer Program for the Macintosh. Cherwell Scientific, Oxford Science Park, Oxford OX4 4GA, UK

621. Alagona G, Ghio C, Monti S (2000) Continuum Solvent Effects on Various Isomers of Bilirubin. Phys Chem Chem Phys 2:4884

622. Alagona G, Ghio C, Agresti A, Pratesi R (1998) Ab Initio Relative Stability of a Few Conformers of Bilirubin in vacuo and in Aqueous Solution (PCM). Int J Quantum Chem 70:395

623. Harmatz D, Blauer G (1975) Optical Properties of Bilirubin-Serum Albumin Complexes in Aqueous Solution. A Comparison Among Albumins from Different Species. Archiv Biochem Biophys 170:375

References 759

624. Beaven GH, d’Albis A, Gratzer WB (1973) The Interaction of Bilirubin with Human Serum Albumin. Eur J Biochem 33:500

625. Woolley PV III, Margaret J, Arias IM (1976) Bilirubin and Biliverdin Binding to Rat Y Protein (Ligandin). Biochim Biophys Acta, Protein Struct 446:115

626. van der Eijke JM, Nolte RJM, Richters VEM, Drenth W (1980) Polymeric Model System for Protein-Bilirubin Interaction. Biopolymers 19:445

627. Marr-Leisy D, Lahiri K, Balaram P (1985) Bilirubin Binding to Polypeptides and Chiral Amines. Int J Peptide Protein Res 25:290

628. Brodersen R (1962) Physical Chemistry of Bilirubin: Binding to Macromolecules and Membranes. In: Heirwegh KPM, Brown SB (eds) Bilirubin, vol I. CRC Press Inc, Boca Raton, Florida, p 75

629. Brodersen R (1986) Aqueous Solubility, Albumin Binding, and Tissue Distribution of Bilirubin. In: Ostrow JD (ed) Bile Pigments and Jaundice. Marcel Dekker, New York, p 157

630. Wennberg RP (1975) The Pathogenesis of Kernicterus: Factors Influencing the Distribution of Bilirubin with Albumin and Tissue. In: Bakken AF, Fog J (eds) Proceedings of a Conference on the Metabolism and Chemistry of Bilirubin and Related Tetrapyrroles. Pediatric Research Institute, Rikshospitalet, Oslo, Norway

631. Jacobsen C (1978) Lysine Residue 240 of Human Serum Albumin Is Involved in High-affinity Binding of Bilirubin. Biochem J 171:453

632. Perrin H, Wilsey M (1971) The Induced Optical Activity of Bilirubin in the Presence of Sodium Deoxycholate. J Chem Soc Chem Commun:769

633. Reisinger M, Lightner DA (1985) Bilirubin Conformational Enantiomer Selection in Chiral Sodium Deoxycholate Chiral Micelles. J Inclusion Phenomena 3:479

634. LeBas G, DeRango C, Tsoucaris G (1982) Chiral Conformation of Bilirubin, Biliverdin and Benzil in Association with Cyclodextrin. In: Szejtli, J (ed) Proceedings of the 1st International Symposium on Cyclodextrins. D Reidel, Dordrecht, The Netherlands, p 245

635. Lightner DA, Gawroński JK, Gawrońska K (1985) Bilirubin Enantiomer Selection by Cyclodextrins. J Am Chem Soc 107:2456

636. Kano K, Tsujino N, Kim M (1992) Mechanisms for Steroid-induced Conformational Enantiomerism of Bilirubin in Protic Solvents. J Chem Soc Perkin Trans II:1747

637. Kano K, Arimoto S, Ishimura T (1995) Conformational Enantiomerism of Bilirubin and Pamoic Acid Induced by Protonated Aminocyclodextrins. J Chem Soc Perkin Trans II:1661

638. Kano K, Yoshiyasu K, Yasuoka H, Hata S, Hashimoto S (1992) Chiral Recognition by Cyclic Oligosaccharides. Enantioselective Complexation of Bilirubin with b-Cyclodextrin through Hydrogen Bonding in Water. J Chem Soc Perkin Trans II:1265

639. Kano K, Yoshiyasu K, Hashimoto K (1990) Molecular Recognition by Saccharides. Asymmetric Complexation Between Bilirubin and Nucleosides. Chem Lett:21

640. Lightner DA, Reisinger M, Landen GL (1986) On the Structure of Albumin Bound Bilirubin. J Biol Chem 261:6034

641. Lightner DA, Wijekoon WMD, Zhang MH (1988) Understanding Bilirubin Conformation and Binding. Circular Dichroism of Human Serum Albumin with Bilirubin and Its Esters. J Biol Chem 263:16669

642. Lightner DA, An JY, Pu Y-M (1987) Circular Dichroism of Bilirubin-Amine Heteroassociation Complexes. Tetrahedron 43:4287

643. Lightner DA, An JY, Pu YM (1988) Circular Dichroism of Bilirubin-Amine Association Complexes. Insights into Bilirubin-albumin Binding. Arch Biochem Biophys 262:543

644. Pu YM, Lightner DA (1989) Intramolecular Exciton Coupling and Induced Circular Dichroism from Bilirubin-Ephedrine Heteroassociation Complexes. Stereochemical Models for Protein Binding. Croatica Chem Acta 62:301

645. Lightner DA, Gawroński JK, Wijekoon WMD (1987) Complementarity and Chiral Recognition: Enantioselective Complexation of Bilirubin. J Am Chem Soc 109:6354

646. Bouvier M, Brown GR (1988) The Induced Optical Activity of Bound Bilirubin. A Review. Can J Spectrosc 33:83

647. Turner EE, Harns MM (1948) Asymmetric Transformation and Asymmetric Induction. Quarterly Rev Chem Soc 1:299

References760

648. Pirkle WH, Hoover DJ (1982) NMR Chiral Solvating Agents. In: Allinger NH, Eliel EL, Wilen SH (eds) Topics in Stereochemistry, vol 13. Wiley Interscience, New York, p 263

649. Lightner DA, Ma J-S (1986) Intramolecular Hydrogen Bonding in Bilirubin bis-tetra-n-Butylam monium Salts. Spectrosc Lett 19:311

650. Lightner DA, An J-Y (1987) Circular Dichroism and Conformation of Bilirubin bis-N,N,N-Trimethyl-a-phen ethylammonium Salts. Spectrosc Lett 20:491

651. Pu YM, Lightner DA (1991) On the Conformation of Bilirubin Dianion. Tetrahedron 47:6163

652. Lightner DA, Trull FR (1983) Intermolecular Hydrogen Bonding and Dimeric Structures in Bilirubin Esters from 1H-NMR Spectroscopy. Spectrosc Lett 16:785

653. Zhang M-H, Lightner DA (1987) Conformation of Bilirubin Esters from Circular Dichroism Spectroscopy. Tetrahedron Lett 28:4033

654. Brower JO, Huggins MT, Boiadjiev SE, Lightner DA (2000) On the Molecularity of Bilirubins and Their Esters and Anions in Chloroform Solution. Monatsh Chem 131:1047

655. Ghosh B, Catalano VJ, Lightner DA (2004) Crystal Structure and Conformation of a Bilirubin Ester. Monatsh Chem 135:1503

656. Trull FR, Ma JS, Landen GL, Lightner DA (1983) Hydrogen Bonding of Bilirubin and Pyrromethenones in Solution. Isr J Chem 23:211

657. Lightner DA, Reisinger M, Wijekoon WMD (1987) Optically Active Pyrromethenone Amides. Exciton Coupling in Hydrogen-bonded Dimers. J Org Chem 52:5391

658. Byun YS, Lightner DA (1991) Exciton Coupling from Dipyrrinone Chromophores. J Org Chem 56:6027

659. Nogales DF, Ma J-S, Lightner DA (1993) Self-association of Dipyrrinones Observed by 2D-NOE NMR and Dimerization Constants Calculated from 1H-NMR Chemical Shifts. Tetrahedron 49:2361

660. Boiadjiev SE, Anstine DT, Lightner DA (1995) Intermolecular Hydrogen Bonding in p Facial Dipyrrinone Dimers as Molecular Capsules. J Am Chem Soc 117:8727

661. Boiadjiev SE, Anstine DT, Maverick E, Lightner DA (1995) Hydrogen Bonding and p-Stacking in Dipyrrinone Acid Dimers of Xanthobilirubic Acids and Chiral Analogs. Tetrahedron: Asymm 6:2253

662. Huggins MT, Lightner DA (2001) Hydrogen-bonded Dimers in Dipyrrinones and Acyl Dipyrrinones. Monatsh Chem 132:203

663. Rebek J Jr (1987) Model Studies in Molecular Recognition. Science 235:1478 664. Rebek J Jr (2009) Molecular Behavior in Small Spaces. Acc Chem Res 42:1660 665. Rebek J Jr (1999) Asymmetric Phenomena in Studies of Encapsulation and Assembly. In:

Palyi G, Zucchi C, Caglioti L (eds) Advances in Biochirality. Elsevier Science, Amsterdam, p 315

666. Gawroński JK, Polonski T, Lightner DA (1990) Sulfoxides as Chiral Complexation Agents. Conformational Enantiomer Resolution and Induced Circular Dichroism of Bilirubins. Tetrahedron 46:8053

667. Trull FR, Shrout DP, Lightner DA (1992) Chiral Recognition by Sulfoxides. Induced Circular Dichroism from Symmetric Mesobilirubin Analogs. Tetrahedron 48:8189

668. Murakami Y, Hayashida O, Nagai Y (1994) Enantioselective Discrimination by Cage-type Cyclophanes Bearing Chiral Binding Sites in Aqueous Media. J Am Chem Soc 116:2611

669. Hayashida O, Matsuura S, Murakami Y (1994) Specific Molecular Recognition by Cage-type Cyclophanes Having a Helically Twisted and Cylindrical Internal Cavity. Tetrahedron 50:13701

670. Chung TW, Cho KY, Nah JW, Akaike T, Cho CS (2002) Chiral Recognition of Bilirubin by Polymeric Nanoparticles. Langmuir 18:6462

671. Yashima E, Fukaya H, Sahavattanapong P, Okamoto Y (1996) Chiral Discrimination of Bilirubin by Cellulose Trisphenylcarbamate Derivatives in Chloroform and in Film. Enantiomer 1:193

672. Bombelli C, Bernardini C, Elemento G, Mancini G, Sorrenti A, Villani C (2008) Concentration as the Switch for Chiral Recognition in Biomembrane Models. J Am Chem Soc 130:2732

References 761

673. Goncharova I, Urbanova M (2007) Bile Pigment Complexes with Cyclodextrins: Electronic and Vibrational Circular Dichroism Study. Tetrahedron: Asymm 18:2061

674. Julinek O, Goncharova I, Urbanova M (2008) Chiral Memory and Self-replication of Porphyrin and Bilirubin Aggregates Formed on Polypeptide Matrices. Supramol Chem 20:643

675. Goncharova I, Urbanova M (2008) Stereoselective Bile Pigment Binding to Polypeptides and Albumins: A Circular Dichroism Study. Anal Bioanal Chem 392:1355

676. Goncharova I, Urbanova M (2009) Vibrational and Electronic Circular Dichroism Study of Bile Pigments: Complexes of Bilirubin and Biliverdin with Metals. Anal Biochem 392:28

677. Berova N, Povalarapu P, Nakanishi K, Woody RW (eds) (2011) Comprehensive Chiroptical Spectroscopy. John Wiley & Sons Inc, New York

678. Kasha M, Rawls HR, El-Bayoumi MA (1965) The Exciton Model in Molecular Spectroscopy. Pure Appl Chem 11:371

679. McRae EG, Kasha M (1964) The Molecular Exciton Model. In: Augenstein L, Mason R, Rosenberg B (eds) Physical Processes in Radiation Biology. Academic Press, New York, p 23

680. Kasha M (1963) Energy Transfer Mechanisms and Molecular Exciton Model for Molecular Aggregates. Radiation Res 20:55

681. Kasha M, El-Bayoumi MA, Rhodes W (1961) Excited States of Nitrogen Base Pairs and Polynucleotides. J Chim Phys Physicochim Biol 58:916

682. Berova N, Nakanishi K (2000) Exciton Chirality Method: Principles and Applications. In: Berova N, Nakanishi K, Woody RW (eds) Circular Dichroism. Principles and Applications, 2nd ed. John Wiley & Sons Inc, New York, p 337

683. Lightner DA (ed) (2005) Exciton Chirality: Fundamentals and Frontiers. Monatsh Chem 136, issue 3

684. Boiadjiev SE, Lightner DA (2005) Exciton Chirality. (A) Origins of and (B) Applications from Strongly Fluorescent Dipyrrinone Chromophores. Monatsh Chem 136:489

685. Matile S, Berova N, Nakanishi K, Fleischhauer J, Woody RW (1996) Structural Studies by Exciton Coupled Circular Dichroism Over a Large Distance: Porphyrin Derivatives of Steroids, Dimeric Steroids, and Brevitoxin. J Am Chem Soc 118:5198

686. Wellman KM, Laur PHA, Briggs WS, Moscowitz A, Djerassi C (1965) Optical Rotatory Dispersion Studies. XCIX. Superposed Multiple Cotton Effects of Saturated Ketones and Their Significance in the Circular Dichroism Measurement of (–)-Menthone. J Am Chem Soc 87:66

687. Boiadjiev SE, Lightner DA (1999) Optical Activity and Stereochemistry of Linear Oligopyrroles and Bile Pigments. Tetrahedron: Asymm 19:607

688. Puzicha G, Pu Y, Lightner DA (1991) Allosteric Regulation of Conformational Enantiomerism. Bilirubin. J Am Chem Soc 113:3585

689. Boiadjiev SE, Person RV, Puzicha G, Knobler C, Maverick E. Trueblood KN, Lightner DA (1992) Absolute Configuration of Bilirubin Conformational Enantiomers. J Am Chem Soc 114:10123

690. Plieninger H, El-Barkawi F, Ehl K, Kohler R, McDonagh AF (1972) Neue Synthese und 14C-Markierung von Bilirubin-IXa. Liebig’s Ann Chem 758:195

691. Corwin AH, Coolidge EC (1952) A Stepwise Porphyrin Synthesis. J Am Chem Soc 74:5196

692. Johnson AW, Kay IT (1961) The Formation of Porphyrins by the Cyclization of Bilenes. J Chem Soc:2418

693. Harris RLN, Johnson AW, Kay IT (1966) A Stepwise Synthesis of Unsymmetrical Porphyrins. J Chem Soc C:22

694. Clezy PS, Liepa AJ (1969) Porphyrins from Electronegatively-substituted Bilenes. J Chem Soc D:767

695. Clezy PS, Salek A (1996) The Chemistry of Pyrrolic Compounds. LXXI. Synthesis of the Ring C and the Ring D Demethyl Analogs of Deoxophylloerythroetioporphyrin (dpep). Aust J Chem 49:265

References762

696. Jackson AH, Smith KM (1973) The Total Synthesis of Pyrrole Pigments. In: ApSimon J (ed) The Total Synthesis of Natural Products. Wiley-Interscience, New York, p 143

697. Hudson MF, Smith KM (1975) Bile Pigments. Chem Soc Rev 4:363 698. Kadish K, Smith KM, Guilard R (eds) (1999) The Porphyrin Handbook, vol I. Academic

Press, New York 699. Kadish K, Smith KM, Guilard R (eds) (2010) Handbook of Porphyrin Science. World

Scientific Publishing Co, Hackensack, New Jersey 700. Plieninger H, Decker M (1956) Eine Neue Synthese für Pyrrolone, Insbesondere für

„Isooxyopsopyrrol” und „Isoopsopyrrol-carbonsäure”. Liebig’s Ann Chem 598:198 701. Plieninger H, Bühler W (1959) Eine Synthese für a,a¢-Unsubstituierten Pyrrole. Angew

Chem 71:163 702. Plieninger H, Lerch U (1966) Totalsynthese Zweier Racemischer Stercobiline-IXa.

Liebig’s Ann Chem 698:196 703. Plieninger H (1968) Synthesen in der Pyrrolon- und Pyrrolreihe. Angew Chem 80:242 704. Plieninger H, Steinsträsser R (1969) Synthese Zweier Vinyl-substituierter Urobiline IXa.

Liebig’s Ann Chem 723:149 705. Plieninger H, Ruppert J (1970) Synthese des (–)-Stercobilins IXa („nat.” Stercobilin) und

Anderer Optisch Aktiver Stercobiline. Liebig’s Ann Chem 735: 43 706. Plieninger H, Ehl K, Tapia A (1970) Gallenfarbstoffsynthesen IV. Die Synthese Optisch

Aktiver Urobiline. Liebig’s Ann Chem 736:62 707. Plieninger H, Ehl K, Klinga K (1971) Gallenfarbstoffsynthesen V. Über Mesobilivioline.

Liebig’s Ann Chem 743:112 708. Brockmann H Jr, Knobloch G, Plieninger H, Ehl K, Ruppert J, Moscowitz A, Watson CJ

(1971) Absolute Configuration of Natural (–)-Stercobilin and other Urobilinoid Compounds. Proc Natl Acad Sci USA 68:2141

709. Preuss I, Plieninger H (1982) Ein Neuer Zugang zu 3,4-Dihydropyrromethenonen als Bausteine für Phytochrom-Modell Verbindungen. Tetrahedron Lett 23:43

710. Plieninger H, Preuss I (1983) Ein Neuer Synthetischer Weg zu Phytochromobilin-ähnlichen Gallenfarbstoffen. Liebig’s Ann Chem:585

711. Böhm H, Gottschall K, Plieninger H (1984) Darstellung Konfigurationsisomerer 3,4-Dihydrobilinsäurederivate als Bausteine für Gallenfarbstoffsynthesen. Liebig’s Ann Chem:1441

712. Gottschall K, Plieninger H (1984) Darstellung des rac-Stercobilins IXa mit der Konfiguration des Naturproduktes Sowie Einer Reihe von Urobilinen, Halbstercobilinen und Stercobilinen Eindeutiger Konstitution und Konfiguration. Liebig’s Ann Chem:1454

713. Gossauer A, Plieninger H (1979) Synthesis, Purification and Characterization of Bile Pigments and Related Compounds. In: Dolphin D (ed) The Porphyrins, vol VI, Biochemistry, Part A. Academic Press, Inc, New York, p 585

714. von Dobeneck H, Brunner E, Sommer U (1977) Das Verhalten von 9-Brom-11H-dipyrromethen-1(10H)-onen in Essigsäure und Über 5-(1-Oxo-1,10-dihydro-11H-dipyrromethen-9-yl)-1H-dipyrromethen-1,9(11H)-dione. Liebig’s Ann Chem:1435

715. Gossauer A, Miehe D (1974) Totalsynthese des Mesobilirhodin-dimethylesters. Liebig’s Ann Chem:352

716. Gossauer A, Kühne G (1977) Stereospezifische Totalsynthesen Diastereomerer Mesobilirhodine und Isomesobilirhodine. Liebig’s Ann Chem:664

717. Gossauer A, Hinze R-P (1978) An Improved Chemical Synthesis of Racemic Phycocyanobilin Dimethyl Ester. J Org Chem 43:283

718. Gossauer A, Weller J-P (1978) Totalsynthese des (+)(4R,16R)- und (–)(4R,16S)-[18-Vinyl]mesourobilin IXa-dimethyl esters. Ber Dtsch Chem Ges 111:486

719. Gossauer A, Klahr E (1979) Totalsynthese des racem. Phycoerythrobilin-dimethylesters. Ber Dtsch Chem Ges 112:2243

720. Gossauer A (1983) Synthetic Methods in Bile Pigment Chemistry. Isr J Chem 23:167 721. Valasinas A, Diaz L, Frydman B, Friedmann HC (1985) Total Synthesis of Urobiliverdin

Isomers. Identification of Bactobilin as Urobiliverdin I. J Org Chem 50:2398

References 763

722. Awruch J, Frydman B (1986) The Total Synthesis of Biliverdins of Biological Interest. Tetrahedron 42:4137

723. Iturraspe JC, Bari S, Frydman B (1989) Total Synthesis of “Extended” Biliverdins. The Relation Between Their Conformation and Their Spectroscopic Properties. J Am Chem Soc 111:1525

724. Iturraspe J, Bari S, Frydman B (1995) Synthesis of Biliverdins with Stable Extended Conformations. Part I. Tetrahedron 51:2243

725. Bari S, Iturraspe J, Frydman B (1995) Synthesis of Biliverdins with Stable Extended Conformations. Part II. Tetrahedron 51:2255

726. Falk H, Grubmayr K (1977) Eine Neue Synthese von C2V-Symmetrisch Substituierten a,b,c,-Bilatrienen. Synthesis:614

727. Boiadjiev SE, Lightner DA (1994) Synthetic Strategies for Understanding Bilirubin Stereochemistry. Synlett:777

728. Boiadjiev SE, Lightner DA (2001) An Enantiomerically Pure Bilirubin. Absolute Configuration of (aR,a¢R)-Dimethylmesobilirubin-XIIIa. Tetrahedron: Asymm 12:2551

729. Boiadjiev SE, Lightner DA (2000) Steric Size in Conformational Analysis. Steric Compression Analyzed by Circular Dichroism Spectroscopy. J Am Chem Soc 122:11328

730. Boiadjiev SE, Lightner DA (2000) Relative Steric Size of SCH3, OCH3 and CH3 Groups from Circular Dichroism Measurements. Chirality 12:204

731. McDonagh AF, Assisi F (1972) The Ready Isomerization of Bilirubin IX-a in Aqueous Solution. Biochem J 129:797

732. McDonagh AF, Assisi F (1972) Direct Evidence for Acid-catalyzed Isomeric Scrambling of Bilirubin-IXa. J Chem Soc Chem Commun:117

733. McDonagh AF (1995) Thermal and Photochemical Reactions of Bilirubin. Ann NY Acad Sci 244:553

734. Bonnett R, McDonagh AF (1970) The Isomeric Heterogeneity of Biliverdin Dimethyl Ester Derived from Bilirubin. Ann NY Acad Sci 244:238

735. Bonnett R, Buckley DG, Hamzetash D, McDonagh AF (1983) Pyrrole Exchange Reactions in the Bilirubin Series. Isr J Chem 23:173

736. Trull FR, Rodríguez M, Lightner DA (1993) A General Method for Synthesizing Unsymmetric from Symmetric Bile Pigments. Synth Commun 23:2771

737. Trull FR, Lightner DA (1988) Synthesis of Unsymmetric Bile Pigments: Mesobilirubin-VIIIa, 17-Desvinyl-17-ethyl-bilirubin-VIIIa and 12-Despropionic Acid-12-ethyl-mesobilirubin-XIIIa. J Heterocycl Chem 25:1227

738. Abbate S, Lebon F, Longhi G, Boiadjiev SE, Lightner DA (2012) Vibrational and Electronic Circular Dichroism of Dimethyl Mesobilirubins-XIIIa. J Phys Chem B 116:5628

739. Pu Y-M, Lightner DA (1991) On the Conformation of Bilirubin Dianion. Tetrahedron 47:6163

740. Pu Y-M, McDonagh AF, Lightner DA (1993) Inversion of Circular Dichroism with a Drop of Chloroform. Unusual Chiroptical Properties of Aqueous Bilirubin-Albumin Solutions. J Am Chem Soc 115:377

741. Pu Y-M, McDonagh AF, Lightner DA (1992) Effect of Volatile Anesthetics on the Circular Dichroism of Bilirubin Bound to Human Serum Albumin. Experientia 48:246

742. Boiadjiev SE, Lightner DA (2000) Chirality Inversion in a Molecular Exciton. J Am Chem Soc 122:378

743. Maisels MJ, McDonagh AF (2008) Phototherapy for Neonatal Jaundice. New Engl J Med 358:920

744. Maisels MJ, Watchko JF (eds) (2001) Neonatal Jaundice. Harwood Academic Publications, Amsterdam

745. Dennery PA, Seidman DS, Stevenson DK (2001) Neonatal Hyperbilirubinemia. New Engl J Med 344:581

746. Chowdury JR, Wolkoff AW, Chowdury NR, Arias IM (2001) Hereditary Jaundice and Disorders or Bilirubin Metabolism. In: Scriver CR, Beaudet AL, Sly WS, Valle D (eds) The

References764

Metabolic and Molecular Bases of Inherited Disease, vol II. McGraw-Hill, Inc, New York, p 3063

747. Ennever J (1988) Phototherapy for Neonatal Jaundice. Photochem Photobiol 47:871 748. Levine R, Maisels MJ (1983) Hyperbilirubinemia in the Newborn. Report of the 85th Ross

Conference on Pediatric Research, Ross Laboratory Publishers 749. Brown AK, McDonagh AF (1980) Phototherapy for Neonatal Hyperbilirubinemia:

Efficacy, Mechanism and Toxicity. In: Barnes LA (ed) Advances in Pediatrics, vol 27, Year Book Medical Publishers, Inc, New York

750. Cremer RJ, Perryman PW, Richards DH (1958) Influence of Light on the Hyperbilirubinaemia of Infants. Lancet 271:1094

751. Dobbs RH, Cremer RJ (1975) Phototheraphy. Arch Dis Childhood 50:833 752. Bergsma D, Blondheim SH (eds) (1976) Bilirubin Metabolism in the Newborn (II).

National Foundation – March of Dimes, New York 753. Neonatal Phototherapy (1982) Bibliography. Olympic Medical Corp, Seattle, Washington 754. Blondheim SH, Lathrop D, Zabriskie J (1960) Diffusible Bilirubin(oid) Produced by

Exposure of Jaundiced Serum to Light. Gastroenterology 38:798 755. Blondheim SH, Lathrop D, Zabriskie J (1962) Effect of Light on the Absorption Spectrum

of Jaundiced Serum. J Clin Lab Med 60:31 756. Blondheim SH, Kaufmann NA (1962) The Effect of Light on the Direct Diazo Reaction of

Conjugated Bilirubin. Pediatrics 65:659 757. Ostrow JD, Hammaker L, Schmid R (1961) The Preparation of Crystalline Bilirubin-C14.

J Clin Invest 40:1442 758. Schmid R, Hammaker L (1963) Metabolism and Disposition of C14-Bilirubin in Congenital

Nonhemolytic Jaundice. J Clin Invest 42:1720 759. Callahan EW Jr, Thaler MM, Karon M, Bauer K. Schmid R (1970) Phototherapy of Severe

Unconjugated Hyperbilirubinemia: Formation and Removal of Labeled Bilirubin Derivatives. Pediatrics 46:841

760. Ostrow JD, Branham RV (1970) Photodecay of Bilirubin in vitro and in the Jaundiced (Gunn) Rat. In: Bergsma D, Hsia DY-Y, Jackson C (eds). Bilirubin Metabolism in the Newborn. Birth Defects: Original Article Series vol VI, no 2. Williams and Wilkins Co, Baltimore, p 93

761. Davies RE, Keohane SJ (1970) Some Aspects of the Photochemistry of Bilirubin. Boll Chim Farm 109:589

762. McDonagh AF, Palma LA, Lightner DA (1982) Phototherapy for Neonatal Jaundice. Stereospecific and Regioselective Photoisomerization of Bilirubin Bound to Human Serum Albumin and NMR Characterization of Intramolecularly Cyclized Photoproducts. J Am Chem Soc 104:6867

763. Ostrow JD, Berry CS, Knodell RG, Zarembo JE (1976) Effect of Phototherapy on Bilirubin Excretion in Man and the Rat. In: Bergsma D, Blondheim SH (eds) Bilirubin Metabolism in the Newborn (II). Birth Defects: Original Article Series, vol XII, no 2. American Elsevier, New York, p 81

764. Kapitulnik J, Blondheim SH, Grunfeld A, Kaufmann NA (1973) Photocomposition of Bilirubin: Ultrafilterable Derivatives. Clin Chim Acta 47:159

765. Kapitulnik J, Kaufmann NA, Blondheim SH (1976) Characteristics of a Photoproduct of Bilirubin Vound in vivo and in vitro, and Its Effect on Bilirubin Binding Affinity of Serum. In: Berk PD, Berlin NI (eds) Chemistry and Physiology of Bile Pigments (Fogarty International Proceedings, no 35). U.S. Government Printing Office, Washington, DC, p 53

766. Ostrow JD, Berry CS, Zarembo JE (1974) Studies on the Mechanism of Phototherapy in the Congenitally Jaundiced Rat. In: Odell GB, Schaffer R, Simopoulos AP (eds) Phototherapy in the Newborn: An Overview. Nat Acad Sci USA, Washington, DC, p 74

767. Ostrow JD (1975) Some Aspects of Bilirubin Photometabolism in vivo. In: Bakken AE, Fog J (eds) Metabolism and Chemistry of Bilirubin and Related Tetrapyrroles. Pediatric Research Institute, Rikshopitalet, Oslo, p 199

References 765

768. Davies RE, Keohane SJ (1973) Early Changes in Light-irradiated Solutions of Bilirubin: A Spectrophotometric Analysis. Photochem Photobiol 17:303

769. Lightner DA, Wooldridge TA, McDonagh AF (1979) Photobilirubin: An Early Bilirubin Photoproduct Detected by Absorbance Difference Spectroscopy. Proc Natl Acad Sci USA 76:29

770. Ostrow JD (1967) Photo-oxidative Derivatives of [14C] Bilirubin and Their Excretion by the Gunn Rat. In: Bouchier IAD, Billing BH (eds) Bilirubin Metabolism. Blackwell Scientific Publications, Oxford, UK

771. Ostrow JD, Branham RV (1970) Photodecomposition of Bilirubin and Biliverdin. Gastroenterology 58:15

772. McDonagh AF (1972) Evidence for Single-oxygen Quenching by Biliverdin-IXa Dimethyl Ester and Its Relevance to Photo-oxidation. Biochem Biophys Res Commun 48:408

773. Ostrow JD (1971) Photocatabolism of Labeled Bilirubin in the Congenitally Jaundiced Gunn Rat. J Clin Invest 50:707

774. Ostrow JD (1976) Effects of Phototherapy on Organic Ion Excretion. 4th Annual Meeting, American Society for Photobiology, February 16-20, 1976, Denver, Abstract WAM-B3, p 60

775. Onishi S, Fujikake M, Ogawa Y, Ogawa J (1976) Photodegradation Products of Bilirubin Studied by High Pressure Liquid Chromatography, Gel Permeation Chromatography, Nuclear Magnetic Resonance and Mass Spectrometry. In: Bergsma D, Blondheim SH (eds) Bilirubin Metabolism in the Newborn (II). American Elsevier, New York, p 41

776. Foote CS, Ching T-Y (1975) Chemistry of Singlet Oxygen. XXI Kinetics of Bilirubin Photooxygenation. J Am Chem Soc 97:6209

777. Lightner DA (1977) Products of Bilirubin Photodegradation. In: Berk PD, Berlin NI (eds) Chemistry and Physiol ogy of Bile Pigments. Proceedings of the Fogarty International Symposium, no 35, p 93

778. McDonagh AF (1971) The Role of Singlet Oxygen in Bilirubin Photo-oxidation. Biochem Biophys Res Commun 44:1306

779. Lightner DA (1974) In vitro Photooxidation Products of Bilirubin. In: Odell GB, Schaffer R, Simopoulos AP (eds) Phototherapy in the Newborn: An Overview. Nat Acad Sci USA, Washington DC, p 34

780. Berry CS, Zarembo JE, Ostrow JD (1972) Evidence for Conversion of Bilirubin to Dihydroxyl Derivatives in the Gunn Rat. Biochem Biophys Res Commun 49:1366

781. Quistad GB (1972) The Photooxidation of Alkylpyrroles and Bilirubin. Ph.D. Dissertation, University of California, Los Angeles

782. Lightner DA, Quistad GB (1972) Methylvinylmaleimide from Bilirubin Photooxidation. Science 175:324

783. Lightner DA, Quistad GB (1972) Hematinic Acid and Propentdyopents from Bilirubin Photooxidation in vitro. Fed Europ Biochem Soc (FEBS) Lett 25:94

784. Lightner DA, Quistad GB (1972) Imide Products from Photo-oxidation of Bilirubin and Mesobilirubin. Nature, New Biol 236:203

785. Lightner DA, Crandall DC (1973) The Photooxygenation of Biliverdin. Tetrahedron Lett:953

786. Bonnett R, Stewart JCM (1972) Singlet Oxygen in the Photo-oxidation of Bilirubin in Hydroxylic Solvents. Biochem J 130:895

787. Bonnett R, Stewart JCM (1972) Photo-oxidation of Bilirubin in Hydroxylic Solvents. Propentdyopent Adducts as Major Products. Chem Commun:596

788. Bonnett R, Stewart JCM (1975) Photooxidation of Bilirubin in Hydroxylic Solvents. J Chem Soc Perkin Trans I:224

789. Chong R, Clezy PS, Liepa AJ, Nichol AW (1969) The Chemistry of Pyrrolic Compounds VII. Synthesis of 5,5¢-Diformyldipyrrylmethanes. Aust J Chem 22:229

790. Lightner DA, Crandall DC, Gertler S, Quistad GB (1973) On the Formation of Biliverdin During Photooxygenation of Bilirubin in vitro. FEBS Lett 30:309

References766

791. Burke MJ, Pratt DC, Moscowitz A (1972) Low-temperature Absorption and Circular Dichroism Studies of Phytochrome. Biochemistry 11:4025

792. Wooldridge TA, Lightner DA (1978) Separation of the III-a, IX-a and XIII-a Isomers of Bilirubin and Bilirubin Dimethyl Ester by High Performance Liquid Chromatography. J Liq Chromat 1:653

793. DiCesare JL, Vandemark FL (1981) High Resolution Preparative LC Separation of Bilirubin Isomers. Chromat Newsletter 9:7

794. Manitto P, Monti D (1981) A Simple Procedure for Preparing Bilirubin-XIIIa. Syn Commun 11:811

795. Ma J-S, Lightner DA (1984) Facile Preparation of Symmetric Bilirubins-IIIa and XIIIa from IXa. J Heterocycl Chem 21:1005

796. Reisinger M, Lightner DA (1985) Large Scale Synthesis of Bilirubin-XIIIa from IXa. J Heterocycl Chem 22:1221

797. Boiadjiev SE, Lightner DA (1997) Stereogenic Competition in Bilirubin Conformational Enantiomerism. Tetrahedron: Asymm 8:2115

798. McDonagh AF (1976) Photochemistry and Photometabolism of Bilirubin-IXa. In: Bergsma D, Blondheim SH (eds) Bilirubin Metabolism in the Newborn (II). Birth Defects: Original Article Series, vol. XII, no 2. American Elsevier, New York, p 30

799. Lund HT, Jacobsen J (1972) Influence of Phototherapy on Unconjugated Bilirubin in Duodenal Bile of Newborn Infants with Hyperbilirubinemia. Acta Paediatrica Scand 61: 693

800. McDonagh AF (1975) Phototherapy and Hyperbilirubinaemia. The Lancet, February 8, 339 801. McDonagh AF (1974) Photochemistry and Photometabolism of Bilirubin. In: Odell GB,

Schaffer R, Simopoulos AP (eds) Phototherapy in the Newborn: An Overiew. Nat Acad Sci USA, Washington, DC, p 56

802. McDonagh AF (1974) Photochemistry and Photometabolism of Bilirubin. In: Brown AK, Showacre J (eds) Phototherapy for Neonatal Hyperbilirubinemia, DHEW Publication no (NIH) 76-1075, p 171

803. McDonagh AF, Palma LA (1977) Mechanism of Bilirubin Photodegradation: Role of Singlet Oxygen. In: Berk PD, Berlin NI (eds) Chemistry and Physiology of Bile Pigments. (Fogarty International Proceedings, No 35) U.S. Government Printing Office, Washington, DC, p 81

804. McDonagh AF (1976) Phototherapy of Neonatal Jaundice. Biochem Soc Trans 4:219 805. Lightner DA (1977) On the Photochemistry of Bilirubin and Related Pyrroles. Photochem

Photobiol 26:427 806. Onishi S, Yamakawa T (1970) Influences to Neonatal Bilirubin Metabolism by Phototherapy.

Acta Paediatrica Jpn 12:36 (English abstracts) 807. Lund HT, Jacobsen J (1974) Influence of Phototherapy on the Biliary Excretion Pattern in

Newborn Infants with Hyperbilirubinemia. J Pediatr 85:262 808. Garbagnati E, Manitto P (1973) A New Class of Bilirubin Photo-derivatives Obtained in

vitro and Their Possible Formation in Jaundiced Infants. J Pediatr 83:109 809. Ostrow JD, Knodell RG, Cheney HG, Berry CS (1974) Effects of Phototherapy on Hepatic

Excretory Function in Man and the Rat. In: Brown AK, Showacre J (eds) Phototheraphy for Neonatal Hyperbilirubinemia. DHEW Publication no (NIH) 76-1075, p 151

810. Lightner DA, Linnane WP III, Ahlfors CE (1984) Bilirubin Photooxidation Products in the Urine of Jaundiced Neonates Receiving Phototherapy. Pediatr Res 18: 696

811. Lightner DA, Linnane WP III, Ahlfors CE (1984) Photooxygenation Products of Bilirubin in the Urine of Jaundiced Phototherapy Neonates. In: Rubaltelli FF, Jori G (eds) Neonatal Jaundice. New Trends in Phototherapy. Plenum Press, New York, p 161

812. Falk H, Grubmayr K, Herzig U, Hofer O (1975) The Configurations of the Isomeric 3,4-Dimethyl-5-(1H)-2,2¢-pyrromethenones. Tetrahedron Lett:559

813. McDonagh AF (1976) Jaundice Phototherapy: Photochemical Aspects. 4th Annual Meeting, American Society for Photobiology, February 16-20, 1976, Denver. Abstract WAM-B1, p 51

References 767

814. Falk AH, Grubmayr K, Hofer O, Neufingerl F (1975) Beiträge zur Chemie der Pyrrolpigmente, 9. Mitt.: Bildung, Struktur und Konfiguration von Z- und E-Arylmethyliden-3,4-dimethyl-3-pyrrolin-2-onen. Monatsh Chem 106:301

815. Lightner DA, Park Y-T (1976) Dye-sensitized Photooxygenation of Oxopyrromethenes Related to Bilirub in. Tetrahedron Lett: 2209

816. Lightner DA, Park Y-T (1977) Synthesis, Photooxidation and Z⇄E Photoisomerization of Benzalpyrrolinones. J Heterocycl Chem 14:415

817. Park Y-T, Lightner DA (1978) Sensitized Photoisomerization of Benzalpyrrolinones. J Kor Chem Soc 22:417

818. Lightner DA, Wooldridge TA, McDonagh AF (1979) Configurational Isomerization of Bilirubin and the Mechanism of Jaundice Phototherapy. Biochem Biophys Res Commun 86:235

819. Lightner DA, Wooldridge TA, McDonagh AF (1979) Geometric Isomerization of Bilirubin-IXa and Its Dimethyl Ester. J Chem Soc Chem Commun:110

820. Pederson AO, Schønheyder F, Brodersen R (1977) Photooxidation of Human Serum Albumin and Its Complex with Bilirubin. Eur J Biochem 72:213

821. McDonagh AF, Ramonas L (1978) Jaundice Phototherapy: Micro Flow-cell Photometry Reveals Rapid Biliary Response of Gunn Rats to Light. Science 201:829

822. Stoll MS, Zenone EA, Ostrow JD, Zarembo JE (1977) Photoisomers of Bilirubin and Their Excretion by the Gunn Rat. 5th Annual Meeting of the American Society for Photobiology, May 11-15, San Juan, Puerto Rico, Abstract SAM-D7, p 97

823. Zenone EA, Stoll MS, Ostrow JD (1977) Mechanism of Excretion of Unconjugated Bilirubin (UCB) During Phototherapy. Gastroenterology 72:A-157, p 1180

824. Roos WT, Weiger HH, Windler SCH, Jones CO (1977) Bilirubin Isomers and Phototherapy. Gastroenterology 73:A-45, p 1243

825. Windler SCH (1840) Ueber das Substitutionsgesetz und die Theorie der Typen. Ann Chem Pharm 33:308

826. Friedman HB (1930) The Theory of Types – A Satirical Sketch. J Chem Educ 7:633 827. Cohen AN, Ostrow JD (1980) New Concepts in Phototherapy: Photoisomerization of

Bilirubin IXa and Potential Toxic Effects of Light. Pediatrics 65:740 828. Stoll MS, Zenone EA, Ostrow JD, Zarembo JE (1979) Preparation and Properties of

Bilirubin Photoisomers. Biochem J 183:139 829. Bonnett R (1981) Oxygen Activation and Tetrapyrroles. Essays in Biochem 17:1 830. Bonnett R (1976) Mechanisms of Photodegradation of Bilirubin. Biochem Soc Trans 4:222 831. McDonagh AF (1976) Phototherapy of Neonatal Jaundice. Biochem Soc Trans 4:219 832. Bonnett R (1984) Recent Advances in the Chemistry of Bile Pigments. In: Rubaltelli FF,

Jori G (eds) Neonatal Jaundice. New Trends in Phototherapy. Plenum Press, New York, p 111 833. Palma LA, McDonagh AF, Lightner DA (1980) Blue Light and Bilirubin Excretion.

Science 208:145 834. McDonagh AF (1981) Phototherapy of Hyperbilirubinemia: Molecular Mechanisms. 9th

Annual Meeting of the American Society for Photobiology, June 14-18, 1981, Williamsburg, Virginia. Abstract TPM 3, p 121

835. Stoll MS, Zenone EA, Ostrow JD (1981) Excretion of Administered and Indigenous Photobilirubins in the Bile of the Jaundiced Gunn Rat. J Clin Invest 68:134

836. Onishi S, Itoh S, Kawade N, Isobe K, Sugiyama S (1979) The Separation of Configurational Isomers of Bilirubin by High Pressure Liquid Chromatography and the Mechanism of Jaundice Phototherapy. Biochem Biophys Res Commun 90:890

837. Onishi S, Kawade N, Itoh S, Isobe K, Sugiyama S (1980) High Pressure Liquid Chromatographic Analysis of Anaerobic Photoproducts of Bilirubin-IXa in vitro and Its Comparison with Photoproducts in vivo. Biochem J 190:527

838. Onishi S, Isobe K, Itoh S, Kawade N, Sugiyama S (1980) Demonstration of a Geometric Isomer of Bilirubin-IXa in the Serum of a Hyperbilirubinaemic Newborn Infant and the Mechanism of Jaundice Phototherapy. Biochem J 190:533

References768

839. Onishi S, Itoh S, Isobe K, Sugiyama S (1981) Photoisomers of Bilirubin in Jaundice Phototherapy. Photomed Photobiol 3:59

840. Stoll MS (1981) Transformations of Bilirubin. Biochemical Society. Tetrapyrrole Discussion Group Meeting on Linear Tetrapyrroles, 10th April, Queen Mary College, London, p 6

841. Isobe K, Onishi S (1981) Kinetics of the Photochemical Interconversion Among Geometric Isomers of Bilirubin. Biochem J 193:1029

842. Isobe K, Itoh S, Onishi S, Yamakawa T, Ogino T, Yokoyama T (1983) Kinetic Study of Photochemical and Thermal Conversion of Bilirubin-IXa and Its Photoproducts. Biochem J 209:695

843. Itoh S, Onishi S (1985) Kinetic Study of the Photochemical Changes of (Z,Z)- Bilirubin-IXa Bound to Human Serum Albumin. Biochem J 226:251

844. McDonagh AF, Palma LA, Trull FR, Lightner DA (1982) Phototherapy for Neonatal Jaundice. Configurational Isomers of Bilirubin. J Am Chem Soc 104:6865

845. Stoll MS, Vicker N, Gray CH, Bonnett R (1982) Concerning the Structure of Photobilirubin II. Biochem J 201:179

846. McDonagh AF, Palma LA (1982) Photometabolism of Bilirubin. Continuous Irradiation of Gunn Rats Leads to a Photostationary Equilibrium Mixture of Pigments in Bile. 10th Annual Meeting of the American Society for Photobiology, June 27-July 1, 1982, University of British Columbia, Vancouver, BC, Canada. Abstract TAM-D5, p 110

847. McDonagh, Lightner DA (1982) Anaerobic Photochemistry of Bilirubin (BR) and Related Compounds. Separation and Characterization of Primary and Secondary Products. 10th Annual Meeting of the American Society for Photobiology, June 27-July 1, 1982, University of British Columbia, Vancouver, BC, Canada. Abstract TAM-D, p 111

848. Falk H, Müller N, Ratzenhofer M, Winsauer K (1982) The Structure of “Photobilirubin”. Monatsh Chem 113:1421

849. Falk H, Grubmayr K, Haslinger E, Schlederer T, Thirring K (1978) Beiträge zur Chemie der Pyrrolpigmente, 24. Mitt. Die Diasteomeren (Geometrisch Isomeren) Biliverdin Dimethylester – Struktur, Konfiguration und Konformation. Monatsh Chem 109:1451

850. Trull FR, Franklin RW. Lightner DA (1987) Total Synthesis of Symmetric Bile Pigments: Mesobilirubin-IVa, Mesobilirubin-XIIIa and Etiobilirubin-IVg. J Heterocycl Chem 24:1573

851. McDonagh AF (1975) Thermal and Photochemical Reactions of Bilirubin-IXa. Ann New York Acad Sci 244:553

852. de Groot JA, van der Steen R, Fokkens R, Lugtenberg J (1982) Synthesis and Photoisomerisation of 2,3,17,18,22-Pentamethyl-10,23-dihydro-1,19-[21H,24H]-bilidione, an Unsymmetrical Bilirubin Model Compound. Recl Trav Chim Pays-Bas 101:219

853. de Groot JA, van der Steen R, Fokkens R, Lugtenberg J (1982) Synthesis and Photochemical Reactivity of Bilirubin Model Compounds. Recl Trav Chim Pays-Bas 101:35

854. McDonagh AF, Palma LA, Lightner DA, Ennever JF, Thaler MM (1983) Why Phototherapy Works. Identification of Bilirubin (BR) Photoproducts in vivo. Pediatric Res 17:326A

855. McDonagh AF (1984) Molecular Mechanisms of Phototherapy of Neonatal Jaundice. In: Rubaltelli FF, Jori G (eds) Neonatal Jaundice. New Trends in Phototherapy. Plenum Press, New York, p 173

856. Bonnett R, Buckley DG, Hamzetash D, Hawkes GE, Ioannou S, Stoll MS (1984) Photobilirubin II. Biochem J 219:1053

857. Bonnett R, Ioannou S (1987) Phototherapy and the Chemistry of Bilirubin. Molec Aspects Med 9: 457

858. Onishi S, Miura I, Isobe K, Itoh S, Ogino T, Yokoyama T, Yamakawa T (1984) Structure and Thermal Interconversion of Cyclobilirubin-IXa. Biochem J 218:667

859. Itoh S, Onishi S (1985) Kinetic Study of the Photochemical Changes of (Z,Z)-Bilirubin-IXa Bound to Human Serum Albumin. Biochem J 226:251

860. Onishi S, Itoh S, Yamakawa T, Isobe K, Manabe M, Toyota S, Imai T (1985) Comparison of the Kinetic Study of the Photochemical Changes of (Z,Z)-Bilirubin-IXa Bound to Human Serum Albumin with That Bound to Rat Serum Albumin. Biochem J 239:561

References 769

861. Onishi S, Itoh S, Isobe K (1986) Wavelength-dependence of the Relative Rate Constants for the Main Geometric and Structural Photoisomerization of Bilirubin-IXa Bound to Human Serum Albumin. Biochem J 236:23

862. Onishi S, Isobe K, Itoh S, Manabe M, Saski K, Fukuzaki R, Yamakawa T (1986) Metabolism of Bilirubin and Its Photoisomers in Newborn Infants During Phototherapy. J Biochem 100:789

863. Onishi S, Itoh S, Isobe K, Ochi M, Kunikata T, Imai T (1989) Effect of the Binding of Bilirubin to Either the First Class or the Second Class of Binding Sites of the Human Serum Albumin Molecule on Its Photochemical Action. Biochem J 257:711

864. McDonagh AF (1983) Mechanism of Action of Phototherapy. Hyperbilirubinemia in the Newborn. Report of the Eighty-fifth Ross Conference on Pediatrics Research, September 1983. Ross Laboratories (publisher), Columbus, OH, p 47

865. McDonagh AF (1985) Light Effects on Transport and Excretion of Bilirubin in Newborns. Ann New York Acad Sci 453:65

866. Ennever JA (1988) Phototherapy for Neonatal Jaundice. Photochem Photobiol 47:871 867. Pratesi R, Agati G, Fusi F (1989) Phototherapy for Neonatal Hyperbilirubinemia.

Photodermatology 6:244 868. McDonagh AF, Lightner DA, Reisinger M, Palma LA (1986) Human Serum Albumin as a

Chiral Template. Stereoselective Photocycli zation of Bilirubin. J Chem Soc Chem Commun:249

869. McDonagh AF, Lightner DA (1985) Mechanisms of Phototherapy of Neonatal Jaundice. Regiospecific Photoisomerization of Bilirubins. In: Sund H, Blauer G (eds) Optical Properties and Structure of Tetrapyrroles. Walter de Gruyter, Berlin, p 297

870. McDonagh AF, Lightner DA (1985) Intramolecular Energy Transfer in Bilirubins. In Bensasson RV, Jori G, Land EJ, Truscott TG (eds). Primary Photo processes in Biology and Medicine. Plenum Press, New York, p 321

871. McDonagh AF, Lightner DA, Agati G (1998) Induction of Wavelength-dependent Photochemistry in Bilirubins by Serum Albumin. Monatsh Chem 129:649

872. Lamola AA (1988) Effects of Environment on Photophysical Processes in Bilirubin. In: Sund H, Blauer G (eds) Optical Properties and Structure of Tetrapyrroles. Walter de Gruyter, Berlin, p 310

873. McDonagh AF, Agati G, Fusi F, Pratesi R (1989) Quantum Yields for Laser Photocyclization of Bilirubin in the Presence of Human Serum Albumin. Dependence of Quantum Yield on Excitation Wavelength. Photochem Photobiol 50:305

874. Agati G, Fusi F, Pratesi R, McDonagh AF (1992) Wavelength-dependent Quantum Yield for Z E Isomerization of Bilirubin Complexed with Human Serum Albumin. Photochem Photobiol 55:185

875. Troup GJ, Agati G, Fusi F, Pratesi R (1996) Photophysics of the Variable Quantum Yield of Asymmetric Bilirubin. Aust J Phys 49:673

876. McDonagh AF, Lightner DA, Agati G (1998) Induction of Wavelength-dependent Photochemistry in Bilirubins by Serum Albumin. Monatsh Chem 129:649

877. Mazzoni M, Agati G, Troup GJ, Pratesi R (2003) Analysis of Wavelength-dependent Photoisomerization Quantum Yields in Bilirubin by Fitting Two Exciton Absorption Bands. J Optics A: Pure Appl 5:S374

878. Zietz B, Gillbro T (2007) Initial Photochemistry of Bilirubin Probed by Femtosecond Spectroscopy. J Phys Chem B 111:11997

879. Plaveskeiĭ VY, Mostovnikov VA, Tret’yahova AI, Mostovnikov GR (2007) Photophysical Processes that Determine the Photoisomerization Selectivity of Z,Z-Bilirubin-IXa in Complexes with Albumins. J Opt Technol 74:446

880. Zunszain PA, Ghuman J, McDonagh AF, Curry S (2008) Crystallographic Analysis of Human Serum Albumin Complexed with 4(Z),15(E)-Bilirubin-IXa. J Molec Biol 381:394

881. Dey SK, Lightner DA (2008) Toward an Amphiphilic Bilirubin. The Crystal Structure of a Bilirubin E-Isomer. J Org Chem 73:2704

References770

882. McDonagh AF, Palma LA, Schmid R (1981) Reduction of Biliverdin and Placental Transfer of Bilirubin and Biliverdin in the Pregnant Guinea Pig. Biochem J 194:273

883. Byun YS, Lightner DA (1991) Synthesis and Properties of a Bilirubin Analog with Propionic Acid Groups Replaced by Carboxyl. J Heterocycl Chem 28:1683

884. McDonagh AF, Lightner DA (1994) Hepatic Uptake, Transport and Metabolism of Alkylated Bilirubin in Gunn Rats and Sprague-Dawley Rats. Cell Molec Biol 40:965

885. Chen Q, Huggins MT, Lightner DA, Norona W, McDonagh AF (1999) Synthesis of a 10-Oxo-bilirubin: Effect of the Oxo Group on Conformation, Transhepatic Transport and Glucuronidation. J Am Chem Soc 121:9253

886. Brower JO, Lightner DA, McDonagh AF (2000) Synthesis of a New Lipophilic Bilirubin. Conformation, Transhepatic Transport and Glucuronidation. Tetrahedron 56:7869

887. Tipton AK, Lightner DA, McDonagh AF (2001) Synthesis and Metabolism of the First Thia-Bilirubin. J Org Chem 66:1832

888. Tipton A, Lightner DA (2002) Crystal Structure and Conformation of a 10-Thia-Bilirubin. Monatsh Chem 133:707

889. Ghosh B, Lightner DA (2003) 10-Thia-Mesobilirubin-XIIIa. J Heterocycl Chem 40:1113 890. Brower JO, Lightner DA, McDonagh AF (2001) Aromatic Congeners of Bilirubin.

Synthesis, Stereochemistry, Glucuronidation and Hepatic Transport. Tetrahedron 57:7813 891. McDonagh AF, Lightner DA, Nogales DF, Norona W (2001) Biliary Excretion of a

Stretched Bilirubin in UGT1A1-Deficient (Gunn) and Mrp2-Deficient (TR–) Rats. FEBS Lett 506:211

892. Boiadjiev SE, Lightner DA (2001) A Water-soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl. Monatsh Chem 132:1201

893. Lightner DA, McDonagh AF (2001) Structure and Metabolism of Natural and Synthetic Bilirubins. J Perinatol 21:S13

894. Lightner DA, McDonagh AF, Kar AK, Norona WS (2002) Hepatobiliary Excretion of Biliverdin Isomers and C10-Substituted Biliverdins in Mrp2-Deficient (TR–) Rats. Biochem Biophys Res Commun 293:1077

895. Ghosh B, Lightner DA, McDonagh AF (2004) Synthesis, Conformation and Metabolism of a Selenium Bilirubin. Monatsh Chem 135:1189

896. McDonagh AF, Lightner DA (2007) Influence of Conformation and Intramolecular Hydrogen Bonding on the Acyl Glucuronidation and Biliary Excretion of Acetylenic bis-Dipyrrinones Related to Bilirubin. J Med Chem 50:480

897. McDonagh AF, Boiadjiev SE, Lightner DA (2008) Slipping Past UGT1A1 and Multidrug Resistance-Associated Protein 2 in the Liver. Effects of Steric Compression and Hydrogen Bonding on the Hepatobiliary Elimination of Synthetic Bilirubins. Drug Metab Dispos 36, 930

898. Kar A, Lightner DA (1998) Synthesis and Properties of Bilirubin Analogs with Conformation-perturbing C(10) tert-Butyl and Adamantyl Groups. Tetrahedron 54:12671

899. Brower JO, Lightner, DA (2001) Fluorophenyl Bilirubins. Synthesis and Stereochemistry. Monatsh Chem 132:1527

900. Kar A, Lightner DA (1998) Synthesis and Properties of C(10)-Isopropyl and Isopropylidene Analogs of Bilirubin. Tetrahedron 54:5151

901. Kar A, Tipton AK, Lightner DA (1999) Crystal Structure and Conformation of a 10-Isopropyl Bilirubin. Monatsh Chem 130:833

902. Xie M, Lightner DA (1993) Synthesis and Unusual Properties of C(10)-gem-Dimethyl Bilirubin Analogs. Tetrahedron 49:2185

903. Xie M, Holmes DL, Lightner DA (1993) Bilirubin Conformation and Intramolecular Steric Buttressing. C(10)-gem-Dimethyl Effect. Tetrahedron 49:9235

904. Tu B, Ghosh B, Lightner DA (2004) The gem-Dimethyl Effect: Amphiphilic Bilirubins. Tetrahedron 60:9017

905. Ghosh B, Catalano VJ, Lightner DA (2004) Syntheses, Crystal Structure and Conformations of 10,10-Spiro-Bilirubins. Monatsh Chem 135:1305

References 771

906. Boiadjiev SE, Lightner DA (2003) Novel Benzoic Acid Congeners of Bilirubin. J Org Chem 68:7591

907. Joesten MD, Schaad LJ (1974) Hydrogen Bonding. Marcel Dekker, Inc, New York 908. Kato Y, Toledo LM, Rebek J Jr (1996) Energetics of a Low Barrier Hydrogen Bond in

Nonpolar Solvents. J Am Chem Soc 118:8575 909. Ducharme Y, Wuest JD (1988) Use of Hydrogen Bonds to Control Aggregation. Extensive,

Self-complementary Arrays of Donors and Acceptors. J Org Chem 53:5787 910. Wash PL, Maverick E, Chiefari J, Lightner DA (1997) Acid-Amide Intermolecular

Hydrogen-bonding. J Am Chem Soc 119:3802 911. Tipton AK, Lightner DA (1999) An Intramolecularly Hydrogen-bonded Dihydrotripyrrinone.

Monatsh Chem 130:425 912. Chen Q, Lightner DA (1998) Hemirubin. An Intramolecularly Hydrogen Bonded Analog

for One-half Bilirubin. J Org Chem 63:2665 913. Huggins MT, Lightner DA (2000) Stereochemistry and Conformational Analysis of

Hemirubin. Tetrahedron 56:1797 914. Huggins MT, Lightner DA (2000) Semirubin. A Novel Dipyrrinone Strapped by Hydrogen

Bonds. J Org Chem 65:6001 915. Huggins MT, Lightner DA (2001) Intramolecular Hydrogen Bonding Between Remote

Termini. Tetrahedron 57:2279 916. Huggins MT, Salzameda NT, Lightner DA (2011) Amide to Acid Hydrogen Bonding. The

Dipyrrinone Receptor. Supramolec Chem 23:226 917. Dey SK, Lightner DA (2009) Amphiphilic Dipyrrinones. Methoxylated [6]-Semirubins.

Tetrahedron 65:2399 918. Boiadjiev SE, Lightner DA (2000) On the Aggregation of Bilirubin Using Vapor Pressure

Osmometry. J Heterocycl Chem 37:863 919. Brower JO, Huggins MT, Boiadjiev SE, Lightner DA (2000) On the Molecularity of

Bilirubins and Their Esters and Anions in Chloroform Solution. Monatsh Chem 131:1047 920. Falk H, Schlederer T, Wolschann P (1981) Beiträge zur Chemie der Pyrrolpigmente, 38.

Mitt. Zur Assoziation von Gallenpigmenten. Monatsh Chem 112: 199 921. Falk H, Müller N (1982) Beiträge zur Chemie der Pyrrolpigmente, 43. Mitt. Die

Temperaturabhängigkeit der Licht-Absorption von Bilirubin und Einigen Seiner Derivate. Monatsh Chem 113:111

922. Holzwarth AR, Langer E, Lehner H, Schaffner K (1980) Absorption Luminescence, Solvent-induced Circular Dichroism and 1H NMR Study of Bilirubin Dimethyl Ester: Observation of Different Forms in Solution. Photochem Photobiol 32:17

923. Crusats J, Delgado A, Farrera JA, Rubires R, Ribó JM (1998) Solution Structure of Mesobilirubin-XIIIa Bridged Between the Propionic Acid Substituents. Monatsh Chem 129:741

924. Ostrow JD, Celic L (1984) Bilirubin Chemistry, Ionization and Solubilization by Bile Salts. Hepatology 4:38S

925. Ostrow JD, Mukerjee P, Tiribelli C (1994) Structure and Binding of Unconjugated Bilirubin: Relevance for Physiological Function. J Lipid Res 35:1715

926. Ostrow JD, Celic L, Mukerjee P (1988) Molecular and Micellar Associations in the pH-Dependent Stable and Metastable Dissolution of Unconjugated Bilirubin by Bile Salts. J Lipid Res 29:33S

927. Carroll L (1898) The Hunting of the Snark. An Agony in Eight Fits. Chatto & Windus, London; reprinted 1941, The Macmillan Company of Canada, Ltd, Toronto

928. Brodersen R (1979) Bilirubin. Solubility and Interaction with Albumin and Phospholipid. J Biol Chem 254:2364

929. Brodersen R (1986) Aqueous Solubility, Albumin Binding, and Tissue Distribution of Bilirubin. In: Ostrow JD (ed) Bile Pigments and Jaundice. Marcel Dekker, New York, p 157

930. Brodersen R (1982) Physical Chemistry of Bilirubin: Binding to Macromolecules and Membranes. In: Heirwegh KPM, Brown SB (eds) Bilirubin, vol I. CRC Press, Inc, Boca Raton, Florida, p 75

References772

931. McDonagh AF (2002) Lyophilic Properties of Protoporphyrin and Bilirubin. Hepatology 36:1028

932. Trull FR, Ma JS, Landen GL, Lightner DA (1983) Hydrogen Bonding of Bilirubin and Pyrromethenones in Solution. Isr J Chem 23:211

933. Gawroński JK, Polonski T, Lightner DA (1990) Sulfoxides as Chiral Complexation Agents. Conformational Enantiomer Resolution and Induced Circular Dichroism of Bilirubins. Tetrahedron 46:8053

934. Trull FR, Shrout DP, Lightner DA (1992) Chiral Recognition by Sulfoxides. Induced Circular Dichroism from Symmetric Mesobilirubin Analogs. Tetrahedron 48:8189

935. Hsieh Y-Z, Morris MD (1988) Resonance Raman Spectroscopic Study of Bilirubin Hydrogen Bonding in Solutions and in the Albumin Complex. J Am Chem Soc 110:62

936. Kanna Y, Arai T, Tokumara K (1993) Photoisomerization of Bilirubins and the Role of Intramolecular Hydrogen Bonds. Bull Chem Soc Jpn 66:1482

937. Lee JJ, Daly LH, Cowger ML (1974) Bilirubin Ionic Equilibria; Their Effects on Spectra and on Conformation. Res Commun Pathol Pharmacol 9:763

938. Hansen PE, Thiessen H, Brodersen R (1979) Bilirubin Acidity. Titrimetric and 13C NMR Studies. Acta Chem Scand B33:218

939. Kidrič J, Mavri J, Podobruk M, Hadži D (1990) Intramolecular Hydrogen Bonding in Acid Malonates. Infrared, NMR and ab initio MO Investigations. J Molec Spectros 237:265

940. Guo J, Tolstoy PM, Koeppe B, Denisov GS, Limbach H-H (2011) NMR Study of Conformational Exchange and Double-well Proton Potential in Intramolecular Hydrogen Bonds in Monoanions of Succinic Acid and Derivatives. J Phys Chem A 115:9828

941. Knell AJ, Johnson B, Hutchinson DW (1972) Intramolecular Hydrogen Bonds in Bilirubin. Digestion 6:288

942. Overbeek JTG, Vink CLJ, Deenstra H (1955) The Solubility of Bilirubin. Recl Trav Chim Pays-Bas 74:81

943. Gray CH, Kulczycka A, Nicholson DC (1961) The Chemistry of the Bile Pigments. Part IV. Spectrophotometric Titration of the Bile Pigments. J Chem Soc:2276

944. Lathe GH (1972) Formation and Excretion of Bilirubin. Essays in Biochem 8:107 945. Krasner J, Yaffe SJ (1973) The Automatic Titration of Bilirubin. Biochem Med 7:128 946. Kolosov IV, Shapovalenko (1977) Acid-Base Equilibria in Solutions of Bilirubin. Zh

Obshch Khim 47:2149 (original article submitted November 14, 1975) 947. Kolosov IV, Shapovalenko EP (1977) Study of Acid-Base Equilibria in Aqueous Solutions

of Bilirubin by the Solubility Method. Zh Obshch Khim 47:2155 948. Lucassen J (1961) The Diazo Reaction of Bilirubin and Bilirubin Glucuronide. Doctoral

dissertation, Rijksuniversiteit Utrecht, p 46 949. McDonagh AF, Lightner DA (1981) New Concepts in Phototherapy. Pediatrics 67:929 950. Cohen AN, Ostrow JD (1981) New Concepts in Phototherapy. Pediatrics 67:930 951. Hahm JS, Ostrow JD, Mukerjee P, Webster CC (1986) Solubility and pKa of Unconjugated

Bilirubin in Aqueous Buffer and Bile Salt Solutions, Determined by Isoextraction from Chloroform. Hepatology 6:1185

952. Farmer RC (1901) A New Method for the Determination of Hydrolytic Dissociation. J Chem Soc 79:868

953. Yonger J, Dang VB (1977) Étude de la Liaison Bilirubine-Albumine par Extraction à l’Acide d’un Solvant non Miscible à l’Eau. Pharmacol Perinatale, INSERM 73:199

954. Irollo R, Casteran M, Dang VB, Yonger J (1979) Étude de la Liaison Bilirubine-Albumine I – Étude in vitro par une Méthode de Partage de la Bilirubine entre une Solution Aqueuse et un Solvant Organique Non Miscible à l’Eau. Ann Biol Clin 37:331

955. Girard M-L, Paologgi F, Frappier F (1965) Détermination de la Bilirubine Extractible par les Solvants: Intérêt de la Méthyl-isobutylcétone. Ann Biol Clin 23:279

956. Moroi Y, Matuura R, Hisadome T (1985) Bilirubin in Aqueous Solution. Absorption Spectrum, Aqueous Solubility, and Dissociation Constants. Bull Chem Soc Jpn 58:1426

957. Tiribelli C, Ostrow JD (1990) New Concepts in Bilirubin Chemistry. Transport and Metabolism: Report of the International Bilirubin Workshop, April 6-8, 1989, Trieste, Italy. Hepatology 11:303

References 773

958. Trull FR, Boiadjiev SE, Lightner DA, McDonagh AF (1997) Aqueous Dissociation Constants of Bile Pigments and Sparingly Soluble Carboxylic Acids by 13C-NMR in Aqueous Dimethyl Sulfoxide: Effects of Hydrogen Bonding. J Lipid Res 38:1178

959. Hahm J-S, Ostrow JD, Mukerjee P, Celic L (1992) Ionization and Self-association of Unconjugated Bilirubin, Determined by Rapid Partition from Chloroform, with Further Studies of Bilirubin Solubility. J Lipid Res 33:1123

960. Tiribelli C, Ostrow JD (1993) New Concepts in Bilirubin Chemistry, Transport and Metabolism: Report of the Second International Bilirubin Workshop, April 9-11, 1992, Trieste, Italy. Hepatology 17:715

961. Hagen R, Roberts JD (1969) Nuclear Magnetic Resonance Spectroscopy. 13C Spectra of Aliphatic Carboxylic Acids and Carboxylate Anions. J Am Chem Soc 91:4504

962. Choi PJ, Petterson KA, Roberts JD (2002) Ionization Equilibria of Dicarboxylic Acids in Dimethyl Sulfoxide as Studied by NMR. J Phys Org Chem 15:278

963. Cistola DP, Small DM, Hamilton JA (1982) Ionization Behavior of Aqueous Short-chain Carboxylic Acids: A Carbon-13 NMR Study. J Lipid Res 23:795

964. Small DM, Cabral DJ, Cistola DP, Parks JS, Hamilton JA (1984) The Ionization Behavior of Fatty Acids and Bile Acids in Micelles and Membranes. Hepatology 4:775

965. Hamilton JA (1994) 13C NMR Studies of the Interactions for Fatty Acids with Phospholipid Bilayers, Plasma Lipoproteins, and Proteins. In: Beckmann N (ed) Carbon-13 NMR Spectroscopy of Biological Systems. Academic Press, Inc, New York, p 117

966. Parks JS, Cistola DP, Small DM, Hamilton JA (1983) Interactions of the Carboxyl Group of Oleic Acid with Bovine Serum Albumin: A 13C-NMR Study. J Biol Chem 258:9262

967. Cistola DP (1985) Physicochemical Studies of Fatty Acids in Model Biological Systems. PhD Dissertation, Boston University. Chem Abstr 105:148490

968. Holmes DL, Lightner DA (1995) Synthesis and Acidity Constants of 13CO2H-labelled Mono and Dipyrrole Carboxylic Acids. pKa from 13C-NMR. Tetrahedron 51:1607

969. Holmes DL, Lightner DA (1996) Synthesis and Acidity Constants of 13CO2H-labelled Dicarboxylic Acid. pKas from 13C-NMR. Tetrahedron 52:5319

970. Holmes DL, McDonagh AF, Lightner DA (1996) On the Acid Dissociation Constants of Bilirubin and Biliverdin. pKa Values from 13C NMR Spectroscopy. J Biol Chem 271:2397

971. McDonagh AF, Phimister A, Boiadjiev SE, Lightner DA (1999) Dissociation Constants of Carboxylic Acids by 13C-NMR in DMSO/Water. Tetrahedron Lett 40:8515

972. Boiadjiev SE, Watters K, Lai B, Wolf S, Welch W, McDonagh AF, Lightner DA (2004) pKa and Aggregation of Bilirubin. Biochemistry 43:15617

973. Mukerjee P, Ostrow JD (1998) Effects of Added Dimethylsulfoxide on pKa Values of Uncharged Organic Acids and pH Values of Aqueous Buffers. Tetrahedron Lett 39:423

974. Mukerjee P, Ostrow JD, Tiribelli C (2002) Low Solubility of Unconjugated Bilirubin in Dimethylsulfoxide-Water Systems; Implications for pKa Determinations. BMC Biochem 3:17

975. Ostrow JD, Mukerjee P (2007) Revalidation and Rationale for High pKa Values of Unconjugated Bilirubin. BMC Biochem 8:7; http://www.biomedcentral.com/1471-2091/8/7

976. Mukerjee P, Ostrow JD (2010) Review: Bilirubin pKa Studies; New Models and Theories Indicate High pKa Values in Water, Dimethylformamide and DMSO. BMC Biochem 11:15; http://www.biomedcentral.com/1471-2091/11:15

977. Dey SK, Lightner DA (2010) Lipid- and Water-soluble Bilirubins. Monatsh Chem 141:101 978. Datta S, Lightner DA (2009) 13CO2H-Labeled Semirubin. Hydrogen Bonding and pKa.

Monatsh Chem 140:1229 979. Rebek J Jr, Duff RJ, Gordon WE, Parris K (1986) Convergent Functional Groups Provide

a Measure of Stereoelectronic Effects at Carbonyl Oxygen. J Am Chem Soc 108:6068 980. Onoda A, Yamada Y, Takeda J, Nakayama Y, Okamura T, Doi M, Yamamoto H, Ueyama

N (2004) Stabilization of Carboxylate Anion with a NH×××O Hydrogen Bond: Facilitation of the Deprotonation of Carboxylic Acid by the Neighboring Amide NH Groups. Bull Chem Soc Jpn 77:321

References774

981. Schwarz B, Drueckhammer D (1995) A Simple Method for Determining the Relative Strengths of Normal and Low-barrier Hydrogen Bonds in Solution: Implications to Enzyme Catalysis. J Am Chem Soc 117:11902

982. Soper AK, Luzar A (1992) A Neutron Diffraction Study of Dimethyl Sulphoxide-Water Mixtures. J Chem Phys 97:1320

983. Vaisman II, Berkowitz ML (1992) Local Structural Order and Molecular Associations in Water-DMSO Mixtures. Molecular Dynamics Study. J Am Chem Soc 114:7889

984. McDonagh AF, Palma L (1981) Bilirubin Hydrate. Hepatol Rapid Lit Rev 11:1670 985. Vega-Hissi EG, Estrada MR, LaVecchia MJ, Pis Diez R (2013) Computational Chemical

Analysis of Unconjugated Bilirubin Anions and Insights into pKa Values Clairification. J Chem Phys 138:035101

986. Gossauer A (2003) Synthesis of Bilanes. In: Kadish KM, Smith KM, Guilard R (eds). The Porphyrin Handbook, vol 13, Academic Press, New York, p 237

987. McDonagh AF, Lightner DA (1991) The Importance of Molecular Structure in Bilirubin Metabolism and Excretion. In: Bock KW, Gerok W, Matern S (eds). Hepatic Metabolism and Disposition of Endo and Xenobiotics (Falk Symposium No. 57), Kluwer, Dordrecht, The Netherlands, chap 5, p 47

988. Shrout DP, Puzicha G, Lightner DA (1992) An Efficient Synthesis of Symmetric Bilindiones. Mesobilirubin-XIIIa and Analogs with Varying Alkanoic Acid Chain Lengths. Synthesis:328

989. Trull FR, Person RV, Lightner DA (1997) Conformational Analysis of Symmetric Bilirubin Analogs with Varying Length Alkanoic Acids. Enantioselectivity by Human Serum Albumin. J Chem Soc Perkin Trans II:1241

990. Chiefari J, Person RV, Lightner DA (1992) Synthesis and Conformation of a Bilirubin Analog with Propionic Acid Side Chains Extended to Un decanoic Acid. Tetrahedron 48:5969

991. Thyrann T, Lightner DA (1996) Synthesis and Properties of a Lipid Bilirubin Analog. Tetrahedron 52:447

992. McDonagh AF, Lightner DA (1994) Hepatic Uptake, Transport and Metabolism of Alkylated Bilirubin in Gunn Rats and Sprague-Dawley Rats. Cell Molec Biol 40:965

993. Pfeiffer WP, Lightner DA (1994) Homorubin. A Centrally Homologated Bilirubin. Tetrahedron Lett 35:9673

994. Nogales D, Anstine DT, Lightner DA (1994) Synthesis and Unusual Properties of Expanded Bilirubin Analogs. Tetrahedron 50:8579

995. Anstine DT (1995) Pentapyrrole Analogs of Bilirubin and Hydrogen Bonding. PhD Dissertation, University of Nevada, Reno

996. Boiadjiev SE, Lightner DA (1997) Synthesis of the First Fluorinated Bilirubin. J Org Chem 62:399

997. Boiadjiev SE, Lightner DA (1998) Altering the Acidity and Solution Properties of Bilirubin. Methoxy and Methylthio Substituents. J Org Chem 63:6220

998. Nikitin EN, Lightner DA (2009) Imploded Bilirubins. Synthesis and Properties of C(10)-nor-Mesobilirubin-XIIIa and Analogs. Monatsh Chem 140:97

999. Tu B, Ghosh B, Lightner DA (2003) A New Class of Linear Tetrapyrroles: Acetylenic 10,10a-Didehydro-10a-homobilirubins. J Org Chem 68:8950

1000. Tu B, Ghosh B, Lightner DA (2004) Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins. Monatsh Chem 135:519

1001. Boiadjiev SE, Holmes DL, Anstine DT, Lightner DA (1995) Synthesis and Unusual Properties of an 8,12-bis-Pivalic Acid Analog of Bilirubin. Tetrahedron 51:10663

1002. Bauman D, Killet C, Boiadjiev SE, Lightner DA, Schönhofer A, Kuball H-G (1996) Study of b,b′-Dimethylmesobilirubin-XIIIa Oriented in a Nematic Liquid Crystal by Linear and Circular Dichroism Spectroscopy. J Phys Chem 100:11546

1003. Boiadjiev SE, Lightner DA (1996) Stereocontrol of Bilirubin Conformation. Tetrahedron: Asymm 7:1309

1004. Boiadjiev SE, Pfeiffer WP, Lightner DA (1997) Synthesis and Stereochemistry of Bilirubin Analogs Lacking Carboxylic Acids. Tetrahedron 53:14547

References 775

1005. Boiadjiev SE, Lightner DA (1999) Intramolecular Hydrogen Bonding and Its Influence on Conformation. Circular Dichroism of Chiral Bilirubin Analogs. Tetrahedron: Asymm 10:2535

1006. Boiadjiev SE, Lightner DA (1997) Exciton Chirality of Bilirubin Homologs. Chirality 9:604

1007. Boiadjiev SE, Lightner DA (2001) Chirality Inversion in the Bilirubin Molecular Exciton. Chirality 13:251

1008. Abbate S, Longhi G, Lebon F, Longhi G, Boiadjiev SE, Lightner DA (2011) ECD and VCD Studies of Dimethylmesobilirubins as Models for Understanding Structural Properties of Bilirubin in Solution. 12th International Congress on Circular Dichroism in Spectroscopy, Oxford, UK

1009. Saresberiensis I (1991) Metalogicon. In: Hall JB, Keats-Rohan KSB (eds) Corpus Christianorum Continuatio Mediaevalis, xcvii, Turnhout: Brepols, Book III, Chap IV. See also: http://abaelard.de/abaelard/060013metalogicon.htm

1010. Salisbury J (1995) The Metalogicon of John Salisbury [Johannes Saresberiensis]: A Twelfth Century Defense of the Verbal and Logical Arts of the Trivium. McGarry DD (English trans). University of California Press, Berkeley

1011. Hijmans van den Bergh A, Snapper I (1913) Die Farbstoffe des Serums. Dtsch Arch klin Med: 540

1012. van den Bergh AAH, Muller P (1916) Über eine Direkte und Eine Indirekte Diazoreaction auf Bilirubin. Biochem Z 77:90

1013. Hijmans van den Bergh A (1918) Die Gallenfarbstoffe im Blute. 1st ed, SC van Doesburgh, Leiden and JA Barth Leipzig; 2nd ed (1928) van Doesburgh, Leiden and Barth, Leipzig

1014. van den Bergh AAH (1954) The Bile Pigment in the Blood. In: Kalmar S (Engl trans), Elton NW (ed) Issue 40 of Medical Laboratories Special Report, Chemical Corps, Army (US) Medical Center, Maryland. Publication Control No 5030-40

1015. Hijmans van den Bergh A (1921) La Recherche de la Bilirubine dans le Plasma Sanguin par la Mèthode de la Reaction Diazoique. Presse Med 14:441

1016. McNee JW (1922) The Use of the van den Bergh Test in the Differentiation of Obstructive Jaundice from Other Types of Jaundice. Brit Med J May 6:716

1017. Cole PG, Lathe GH, Billing BH (1954) Separation of Bile Pigments of Serum, Bile and Urine. Biochem J 57:514

1018. Billing BH, Lathe GH (1956) The Excretion of Bilirubin as an Ester Glucuronide, Giving the Direct van den Bergh Reaction. Biochem J 63:6P

1019. Billing BH, Cole PG, Lathe GH (1957) The Excretion of Bilirubin as a Diglucuronide Giving the Direct van den Bergh Reaction. Biochem J 65:774

1020. Schmid R (1956) Glukuronsäure-konjugiertes Biulirubin, das «direkt reagierende» Bilirubin in Serum, Harn und Galle. Schweizerischen Medizin Wachenschr 86:775

1021. Schmid R (1956) Direct-Reacting Bilirubin, Bilirubin Glucuronide, in Serum, Bile, and Urine. Science 124:76

1022. Schmid R (1957) Identification of Direct-Reacting Bilirubin as Bilirubin Glucuronide. J Biol Chem 229:881

1023. Talafant E (1956) Properties and Composition of the Bile Pigment Giving a Direct Diazo Reaction. Nature 178:312

1024. Talafant E, Appelf G (1967) The Nature and Properties of the ‘Ether-Extractable’ Bile Pigment of Serum. In: Bouchner IAD, Billing B (eds) Bilirubin Metabolism. Blackwell, Oxford, UK, p 103

1025. Pirone C, Quirke JME, Priestap HA, Lee DW (2009) Animal Pigment Bilirubin Discovered in Plants. J Am Chem Soc 131:2830

1026. Pirone C, Johnson JV, Quirke JME, Priestap HA, Lee D (2010) The Animal Pigment Bilirubin Identified in Strelizia reginae, the Bird of Paradise Flower. HortScience 45:1411

1027. Falk H, Marko H (1991) Reduction of Bilindione-10-thiol Adduct as a Model of the Reduction Step of the Biliverdin Reductase System. Monatsh Chem 122:319

References776

1028. Ma Q, Hua H-H, Chen Y, Liu B-B, Krämer AL, Scheer H, Zao K-H, Zhou M (2012) Rising Tide of Blue-absorbing Biliprotein Photoreceptors: Characterization of Seven Such Bilin-binding GAF Domains in Nostoc sp. PCC7120. Fed Eur Biochem Soc (FEBS) doi: 1111/febs. 12003

1029. Stocker R, Yamamoto Y, McDonagh AF, Glazer AN, Ames BN (1987) Bilirubin Is an Antioxidant of Possible Physiological Importance. Science 235:1043

1030. Stocker R, Glazer AN, Ames BN (1987) Antioxidant Activity of Albumin-Bound Bilirubin. Proc Natl Acad Sci USA 84:5918

1031. Stocker R, McDonagh AF, Glazer AN, Ames BN (1990) Antioxidant Activities of Bile Pigments: Biliverdin and Bilirubin. Methods Enzymol 186:301

1032. Baranano DE, Rao M, Ferris CD, Snyder SH (2002) Biliverdin Reductase: A Major Physiologic Cytoprotectant. Proc Natl Acad Sci USA 99:16093

1033. Sedlak TW, Saleh M, Higginson DS, Paul BD, Juluri KR, Snyder SH (2009) Bilirubin and Glutathione Have Complementary Antioxidant and Cytoprotective Roles. Proc Natl Acad Sci USA 106:5171

1034. Sedlak TW, Snyder SH (2009) Circling the Wagons for Biliverdin Reductase. J Biol Chem 284:le 11

1035. Stocker R (2004) Antioxidant Activities of Bile Pigments. Antioxid and Redox Signal 6:841

1036. Stocker R (2005) Antioxidant Defense Mechanisms by Heme Oxygenase and Bile Pigments. In: Otterbein LE, Zuckerbraun BS (eds) Heme Oxygenase. Nova Science Publishers, Inc, New York, p 313

1037. Maghzal GJ, Leck M-C, Collinson E, Li C, Stocker R (2009) Limited Role for the Bilirubin-Biliverdin Redox Amplification Cycle in the Cellular Antioxidant Protection by Biliverdin Reductase. J Biol Chem 284:29251

1038. McDonagh AF (2010) The Biliverdin-Bilirubin Antioxidant Cycle of Cellular Protection: Missing a Wheel? Free Rad Biol Med 49:814

777D.A. Lightner, Bilirubin: Jekyll and Hyde Pigment of Life, Progress in the Chemistry of Organic Natural Products, Vol. 98, DOI 10.1007/978-3-7091-1637-1, © Springer-Verlag Wien 2013

AAbbate S, 519, 521, 763, 775Abel JJ, 182, 185, 186, 743Adler E, 751Adloff JP, 112, 740Agati G, 769Agresti A, 488, 758Agricola, 216Ahlfors CE, 545, 766Akaike T, 760Alagona G, 488, 758Allegret A, 454, 754Allinger NH, 760Ames BN, 776Amman H, 750An JY, 759, 760Andersag H, 326, 750, 751Anderson HJ, 744Anderson T, 198, 250, 744Andrenacus JG, 50Anft B, 744Ankli P, 439, 753Anschütz R, 11, 353Anstine DT, 488, 499, 607, 760, 774Antina EV, 735Appelf G, 775Arai T, 772Arias IM, 759, 763Arimoto S, 759Aronheim B, 213, 745Arouet FM, 10Asahina Y, 281, 282, 748Assisi F, 753, 763Astrup T, 589Augenstein L, 761Auwers K, 220, 669, 670, 745

Avogadro A, 5, 112Awruch J, 763

BBader A, 10Baeyer JFWA von, 11, 112, 199, 216, 238,

239, 251, 262, 358, 744, 745Bailly M, 754Bakken AF, 754, 759Balaram P, 759Barañano DE, 755, 776Bari S, 763Barnes JC, 758Bartholomäus E, 281, 284, 291, 680, 684, 688,

689, 748, 749Barton DHR, 434Bauer K, 764Bauman D, 774Beaudet AL, 763Beaven GH, 759Beck PD, 443Becker W, 754Beckmann EO, 184, 251, 743Beer A, 152, 742Beller H, 320, 749Benedict FG, 188Bensasson RV, 769Bergsma D, 756, 764, 765Berk PD, 443, 754, 764–766Berkowitz ML, 774Berlin NI, 764–766Bernardini C, 760Berova N, 499, 761Berry CS, 764–766Berthelot M, 210

Author Index

Author Index778

Berthollet CL, 18Berzelius JJ, 18, 20, 22, 24–27, 29–50, 52, 58,

60, 63, 73, 74, 89, 630, 631, 632, 635, 637, 737, 738

Bildsøe H, 755Billimona F, 755Billing BH, 443, 529, 619, 753, 775Bills CE, 736Biltz H, 438Bischoff CA, 212, 214, 669, 744, 745Blacha M, 754Blacha-Puller M, 754Black PS, 754Blackwood JE, 755Blanckaert N, 752Blauer G, 458– 460, 467–475, 488, 489, 501,

756–758, 769Bley LF, 52, 54, 739Blömer A, 747Blondheim SH, 528, 756, 764, 765Bloomer JR, 443Bock KW, 774Böhm H, 762Boiadjiev SE, 499, 516, 519, 522, 609,

612–615, 758, 760, 761, 763, 766, 770–775

Bombelli C, 760Bonnett R, 371, 400, 411, 412, 426, 443, 444,

446, 454, 460, 465, 480, 537, 546, 548, 553, 573–575, 594, 596, 751, 752, 754, 763, 765, 767, 768

Borkenstein A, 754Bouchier IAD, 753, 765Bouvier M, 759Bramley RK, 443Branham RV, 530, 532, 764, 765Breasted JH, 736Breathnach CS, 743Bredfeldt J, 752Briggs WS, 761Brockbank EM, 736Brockmann H Jr, 762Brodersen R, 440, 455, 456, 550, 589, 590, 595,

598, 599, 603, 753, 759, 767, 771, 772Brønsted JN, 589, 598Brower JO, 611, 760, 770, 771Brown AK, 764, 766Brown AP, 195, 743Brown GR, 759Brown SB, 443, 735, 759, 771Brown SP, 757Brücke EW Ritter von, 59–62, 66, 71, 73, 74,

90, 91, 94, 95, 100, 111, 133, 175, 634, 635, 637, 739

Bruckenstein S, 756Brunner E, 457, 753, 762Buckley DG, 763, 768Bugge-Asperheim B, 440, 455, 753Bühler W, 762Bunsen RWE, 149, 742Burgstahler AW, 493Burke MJ, 443, 452, 755, 766Busk G, 64Bysshe Shelley P, 20Byun YS, 760, 770Cabral DJ, 773

CCadet de Grassicourt LC, 12Cadet LC, 736Caglioti L, 760Callahan EW Jr, 764Campbell JFF, 158, 740Cannizzaro S, 112Capranica S, 166Carey MC, 587Carroll L, 588, 771Carson ER, 443Cason J, 744Casteran M, 772Catalano VJ, 760, 770Cattadori F, 230, 677, 746Cavanaugh GW, 188Caventou JB, 38, 738Celic L, 599, 771, 773Celsus, Aulus Cornelius, 3Chedekel MR, 443Chen J, 741Chen QQ, 376, 608, 751, 752, 770, 771Chen Y, 776Cheney HG, 766Cheng LJ, 376, 751, 752Chevreul ME, 14, 29–31, 35, 41, 65, 433,

625, 736Chiefari J, 605, 771, 774Ching TY, 765Cho CS, 760Cho KY, 760Choi PJ, 773Chong R, 765Chowdury JR, 763Chung TW, 760Ciamician GL, 250, 747Cistola DP, 773Claisen L, 216, 745Clezy PS, 517, 537, 761, 765Coe T, 12, 51, 736

Author Index 779

Cohen AN, 596, 767, 772Cohen JB, 740Cole PG, 619, 775Collinson E, 776Compernolle F, 752Conrad M, 217, 745Conradi BGF, 14, 736Coolidge EC, 761Corwin AH, 761Corwin E, 517Cowger ML, 594, 772Crandall DC, 765Cranmer T 50Craven R, 736Cremer RJ, 764Crist BV, 443Crum Brown A, 11Crusats J, 771Cullen DL, 754Cullen R, 752Curran JO, 29, 35, 41, 737Curry S, 769Czerny A, 618

Dd’Albis A, 759Dallas JL, 559Dalton J, 5, 112Daly, 594Daly LH, 772Damewood JR Jr, 758Dang VB, 772Darlak RS, 756Darwin C 57Datta S, 601, 773Davies JE, 444, 754Davies RE, 530, 531, 548–550, 764, 765Day GE, 43de Groot JA, 768De Rango, 454Decker M, 452, 753, 762Deenstra H, 595, 772Deisenhofer J, 5Delgado A, 771Delisle A, 213, 745Delius HF, 14, 736Demarçay MH, 25–28, 35, 37, 41, 624, 625,

628, 737Democritus, 4Denisov GS, 772Dennery PA, 763Dennstedt M, 250, 252, 747DeRango C, 754, 759

Desaga P, 149Dessaigne M, 217, 745Deutsche CW, 756Dey SK, 575, 610, 769, 771, 773Diaz L, 762DiCesare JL, 766Dietrich GS, 14, 736Djerassi C, 426, 433, 756, 761Dobbs RH, 764Dobeneck H von, 440, 457, 517, 753, 762Doi M, 773Dolphin D, 735Dønstrup S, 755Dormann E, 256, 285, 689, 747Dörner T, 463, 757Draper FW, 740Drenth W, 759Drueckhammer D, 601, 774Ducharme Y, 582, 583, 771Duff RJ, 773Dulk FP, 35, 738Dulong PL, 112, 208Dumas JPA, 4, 89, 654Duppa BF, 745Durham L, 559Dwight T, 740

EEbers G, 735Edward VI, 50Ehl K, 761, 762Ehrlich P, 192, 253Einstein A, 5Eismayer K, 697, 749, 697El-Barkawi F, 761El-Bayoumi MA, 761Elemento G, 760Eliel EL, 760Elton NW, 775Ennever JA, 769Ennever JF, 768Erlenmeyer E, 10Eschenmoser A, 310Estrada MR, 774Everts S, 740Ewald CA, 86, 740

FFalk A, 758, 767Falk H, 3, 310, 376, 444, 446, 447, 452, 453,

467, 477–479, 484, 501, 517, 543, 545–548, 553, 560, 597, 604, 621, 735,

Author Index780

749, 751, 752, 754, 755, 758, 763, 766, 768, 771, 775

Farmer RC, 597, 772Farrar WV, 738Farrera JA, 771Faulkner W, 622Favini G, 477, 758Fehling H von, 10Ferris CD, 755, 776Fieser LF, 753Fieser M, 753Fink H, 747Fischer E, 11, 19, 238, 251, 263, 264Fischer H, 1, 5, 23, 24, 87, 182, 194, 233,

236–239, 248, 251, 256, 271–441, 444, 448–452, 454, 458, 433, 470, 517, 525–528, 536, 539, 552, 560, 561, 603–605, 621, 680–684, 688–699, 704–712, 717, 723–732, 735, 740, 748–752

Fischer M, 748Fischer N, 757Fittig WR, 199, 212–214, 669, 744, 745Fleischhauer J, 761Flodgaard H, 440, 455, 753Fog J, 440, 451, 455, 456, 753, 754, 759Fokkens R, 768Foote CS, 534, 765Ford RA, 520, 523Forino R, 443Fourcroy AF le Comte de, 10, 13, 17, 20, 21,

24, 35, 51, 114, 624, 736, 737Fowweather FS, 753Frank GW, 756Frank S, 757Frankenberg N, 755Frankland E, 745Franklin RW, 604, 768Franz Ferdinand, Archduke, 262, 621Franz II (Franz Josef Karl), 617, 621Franz Joseph I, 50Frappier F, 772Fraunhofer J von, 150, 154Frerichs FT von, 57, 67, 70–78, 82–84, 88,

90–95, 105, 109, 125, 175, 253, 633, 637, 639, 640, 649, 739

Fresenius, 184Freudenberg K, 438, 449Friedman HB, 767Friedmann HC, 762Frommherz C, 35Fröwis W, 752Frydman B, 517, 762, 763Fujikake M, 765

Fukaya H, 760Fukuzaki R, 769Funke O 73, 74, 195, 739, 743Furttenbach J, 365Fusi F, 769

GGalen, 3Galler H, 228Galletti G, 51Gamgee A, 179, 743Garbagnati E, 766Garrod AE Sir, 162–164, 172, 660, 709, 742Garvie RC, 752Gauss J, 757Gawrońska K, 489, 759Gawroński JK, 489, 493, 497, 759, 760, 772Gay-Lussac, JL, 4, 10, 18Gergely S, 446, 754Gerok W, 774Gertler S, 765Geuther A, 216, 251, 745Ghio C, 488, 758Ghosh B, 488, 606, 608, 760, 770, 774Ghuman J, 769Gillbro T, 769Girard ML, 598, 733, 772Gladys CL, 755Glaser F, 212, 213, 744Glazer AN, 776Gloxhuber C, 467, 757Gmelin L, 15, 16, 17, 20, 24, 25, 27, 28,

30–34, 37, 40–42, 46–49, 51, 53, 55, 59–61, 63, 65–67, 70, 77, 79, 80, 89, 98, 112, 121, 136, 149, 175, 181, 433, 619, 625–628, 631, 633, 635, 667, 715–718, 721, 736, 738

Goldmann H, 746Gomes DE, 443Goncharova I, 497, 761Gordon AJ, 520, 523Gordon WE, 773Gossauer A, 517, 604, 736, 754, 762, 774Gottlieb J, 217Gottschall K, 762Gower RP, 744Gratzer WB, 759Gray CH, 433, 439–441, 443, 451, 470, 553,

573, 594, 752, 753, 755, 757, 768, 772Gren FAC, 14, 736Grimm F, 162, 742Grob CA, 439, 753Gross EM, 753

Author Index 781

Gross PLK, 430, 753Grubmayr K, 446, 754, 755, 758, 763,

766–768Grunewald JO, 393, 752Grunfeld A, 764Gugert H, 35Guilard R, 762, 774Guo J, 772Gurker H, 754Gurst JE, 756Gust D, 758

HHaas R, 749Haas K, 228, 229Haberland HW, 393, 402–404, 407, 430, 724,

725, 752Hadži D, 772Hagen R, 773Hahm JS, 598, 599, 772, 773Hahn A, 749Hahn O, 238, 239, 746Halbach H, 757Halbig P, 322, 323, 750Hall JB, 775Haller A von, 13, 15, 51, 114, 736Hamilton JA, 600, 773Hammaker L, 764Hamzetash D, 763, 768Hancock F, 443, 460, 594, 756Hansen AaE, 447, 474, 595, 757Hansen PE, 755, 772Harada N, 474, 501, 757Harmatz D, 756, 758Harns MM, 759Harries C, 746Harris RLN, 492, 761Hartmann P, 752Hartmut M, 5Hashimoto K, 759Hashimoto S, 759Haslinger E, 755, 768Hassel O, 434Hata S, 759Haurowirtz F, 337, 707Hawkes GE, 768Hawkinson V, 753Hayashida O, 760Haydn, 617Heeß W, 749Hefelfinger DT, 756Hein JA, 48, 52–56, 111, 633, 739Heine H, 51

Heintz WH, 41, 46–50, 52, 54–57, 60, 62, 94, 100, 101, 111, 114, 115, 129, 130, 140, 175, 177, 631, 635, 642, 650, 738

Heirwegh KPM, 735, 752, 759, 771Heller JF, 49, 173, 632Hemmerich P, 457, 474, 756Henry VIII, 50Hermann L, 86, 740Hermann W, 355Herrmann M, 749Herzig U, 755, 766Hess K, 747Hess R, 278, 279, 282, 353, 378, 388, 389,

400, 401, 407, 723, 751Hetper J, 746Heuermann G, 15, 736Heynsius A, 158, 740Heyse M, 750Higginson DS, 776Hijmans van den Bergh A, 775Hilditch TP, 745Hilmer H, 709, 751Hinze RP, 762Hippocrates of Cos, 3Hirsch P, 747Hofer O, 446, 477, 754, 755, 758, 766, 767Hoffman von Fallersleben AH, 617Hofmann A von, 10Hofmann AW, 214, 686Höllbacher G, 758Holm F, 85, 86, 740Holmes DL, 600, 606, 613, 770, 773, 774Holmes FL, 18, 737Holzwarth AR, 771Home E, 62, 63, 635, 739Hönigschmid O, 429, 732Hoover DJ, 760Hopkins FG Sir, 162–164, 172, 660, 742Hoppe F, 740Hoppe-Seyler EFI, 79, 80, 85, 86, 88, 150,

154, 162, 176, 177, 195, 196, 198, 204, 219, 665, 669, 742–744

Hori A, 754Hornig LS, 358Howe RB, 443Hsia DYY, 764Hsieh YZ, 772Hua HH, 776Huber R, 5Hudson MF, 762Hüfner G von, 19, 193, 662Huggins MT, 586, 587, 755, 760, 770, 771Hünefeld FL, 194, 743Hunter MJ, 472, 757

Author Index782

Hursthouse MB, 444, 754Hutchinson DW, 443, 452, 456, 460, 594, 595,

602, 754–756, 772

IIhde AJ, 17, 736Imai T, 768, 769Ioannou S, 768Irollo R, 772Ishimura T, 759Isobe K, 567, 767–769Itoh S, 767–769Iturraspe JC, 763

JJackson AH, 443, 762Jackson C, 764Jackson JR, 443Jacobsen C, 759Jacobsen J, 543, 548, 550, 551, 766Jaffe M, 84, 86, 88, 145, 154–162, 186, 196,

656, 661, 662, 740, 742Jakobsen JH, 447, 755Jayne HW, 745Jellinek E, 752Jellinek K, 752Jellum E, 440, 451, 455, 456, 753Jin S, 751, 752Joachim H, 735Joesten MD, 771John of Salisbury (Johannes Parvus), 615Johnson AW, 517, 761Johnson B, 443, 456, 594, 754–756, 772Johnson JV, 775Johnson WB, 736Johnson WS, 433, 753Jolles A, 164–171, 660, 742Jones CO, 552, 767Jones EA, 443Jones PM, 757Jorde C, 444, 754Jori G, 766, 767, 769Joule JA, 755Julinek O, 761Juluri KR, 776

KKadish KM, 762, 774Kalmar S, 775Kanna, 593Kanna Y, 772

Kano K, 489, 759Kapitulnik J, 531, 764Kaplan D, 453, 461, 462, 464, 477, 591–593,

755, 757Kar A, 607, 770Karon M, 764Kasha M, 501, 761Kato Y, 771Kauffman GB, 112, 740Kaufmann NA, 764Kawade N, 767Kay IT, 756, 761Keana JFW, 433, 753Keats J, 20Keats-Rohan KSB, 775Kekulé von Stradonitz FA, 10, 11, 112, 121,

659, 736, 743Keohane SJ, 530, 531, 548, 549, 764, 765Kidrič J, 601, 772Killet C, 774Kim M, 759Kimmich K, 750King TE, 458, 472, 756King TS, 756Kingzett CT, 86, 740Kirchhoff GR, 149Kistiakowsky GB, 196, 662Kjeldahl JGCT, 4, 19, 190Klahr E, 762Klarer J, 323, 712, 750Klinga K, 762Klyne W, 757Knell AJ, 443, 456, 460, 594, 754–756, 772Knipp B, 463, 757Knobler C, 761Knobloch G, 762Knodell RG, 764, 766Knorr L, 238, 250, 251, 278, 747Köbner E, 220, 669, 670Koeppe B, 772Kohler R, 761Kohlrausch WG, 742Kolbe H, 184Kölle M, 220, 669, 670, 672Kolosov IV, 595, 772Kopp HFM, 10Köst HP, 443Krämer AL, 776Krannich W, 747Krasner J, 594, 772Kratky C, 444, 754Krogh-Hansen J, 440, 455, 753Krueger WC, 756Kuball HG, 774

Author Index 783

Kuenzle CC, 442, 443, 452, 457, 458, 460–462, 474, 754–756

Kufer W, 427, 752, 753Kuhn R, 735Kühne FW, 69, 71–74, 78–85, 88, 638–640, 739Kühne G, 762Kulczycka A, 753, 772Kumar KS, 537Kunikata T, 769Kürzinger A, 379Küster H, 750Küster W, 173, 174, 179, 182, 190–194,,

200–244, 246, 252, 257, 263–268, 274, 275, 277, 283, 292, 297–308, 314, 319–355, 357, 359, 362, 412, 439, 525, 545, 621, 661, 669–671, 676, 689, 693, 700–704, 708–711, 742–750

LLagarius JG, 755Lagrange JL Comte de, 10Lagrangia GL, 10Lahiri K, 759Lai B, 773Lamatsch W, 344, 710Lamola AA, 769Land EJ, 769Landen GL, 758–760, 772Landois L, 740Landolt A, 744Lange H, 747Langer E, 771Lassaigne JL, 33, 208, 627, 744Lathe GH, 594, 619, 772, 775Lathrop D, 764Laur PHA, 761Lauroguais, 216LaVecchia MJ, 774Lavie E, 756, 757Lavoisier AL de, 4, 9, 10, 11, 18, 342, 736LeBas G, 445, 454, 461, 489, 754, 759Lebon F, 763, 775Leck MC, 776Lee DW, 775Lee JJ, 594, 772Legg JW, 49, 52, 407, 439, 451, 738, 751Lehmann CG, 47, 77, 638, 738Lehner H, 446, 755, 771Lemberg R, 353, 390, 391, 400, 406, 407, 409,

423, 434, 438, 441, 449–451, 453, 454, 465, 751–753

Lenhart M, 757Leodolter A, 758

Lerch U, 762Leucippus, 4Leuret F, 33, 627Levere TH, 18, 737Levine R, 764Lewis GN, 392Li C, 776Lichtenwald H, 752Liebermann M, 251Liebig J von, 4, 10, 18, 19, 26–29, 41, 42, 44,

71, 89, 113, 173, 181, 199, 358, 552, 737, 738, 745

Liepa AJ, 761, 765Lightner DA, 405, 412, 443, 446, 454, 463,

477, 479, 488, 506, 517, 527, 533–539, 543–551, 555, 557, 558, 560, 567, 568, 575, 583, 587, 591, 596, 600, 601, 604, 609, 613, 615, 735, 740, 752, 754–761, 763–775

Lim CK, 443Limbach HH, 772Lindner F, 750Linnane WP III, 545, 766Linstead RP, 444Lisler MW, 752Liu BB, 776Liu YY, 751, 752Loening K, 755Loir Dr, 25, 51, 737Longhi G, 763, 775Lord Byron, GG, 20Loschmidt JJ, 11Lowman O, 745Loy E, 749Lucassen J, 772Ludwig KFW, 71Lugtenberg J, 566, 768Lund HT, 543, 548, 550, 551, 766Luzar A, 774Lychnell LP, 626

MMa JS, 136, 376, 426, 427, 583, 741, 751, 752,

758, 760, 766, 772Ma Q, 776Mackey W, 431Macquer PJ, 14, 736Magauer K, 755Maghzal GJ, 776Maisels MJ, 763, 764Maly RL, 50, 90, 93, 132, 133–179, 181,

184–186, 190–196, 200–206, 265, 658, 661–663, 665, 682, 740–742

Author Index784

Manabe M, 768, 769Mancini G, 760Mangani S, 754Manitto P, 443, 445, 447, 452, 460, 476, 477,

490, 754–758, 766Marchelewski L, 243, 244, 746Margaret J, 759Margulies L, 758Mark F, 757Marko H, 775Marr-Leisy D, 759Marx K, 29Mason R, 761Matern S, 774Matile S, 499, 761Matsuura S, 760Matuura R, 772Matysik J, 757Mauguen Y, 754Maverick E, 583, 760, 761, 771Mavri J, 772Mayer O, 489Mazur Y, 758Mazzoni M, 769McClellan AL, 753McDonagh AF, 136, 371, 400, 411, 412, 426,

427, 443, 445, 454, 467, 517, 527, 531, 533, 537–558, 560, 567, 568, 575, 590, 596, 604, 622, 735, 741, 751–753, 755, 761, 763–770, 772–774, 776

McGarry DD, 615McNee JW, 775McRae EG, 761Mendeleev DI, 214Merklein F, 108Merzbacher S, 746Metz S, 758Metzger O, 672Metzroth T, 757Meyenburg F von, 220, 669, 670, 745Meyer EF Jr, 754Meyer P, 748Meyer ESC von, 184Meyer-Betz F, 748Mezger O, 228Michael A, 214–216, 226, 745Miehe D, 762Miller CP, 589Mills K, 755Mislow K, 479, 758Miura I, 768Moffitt W, 756Monti D, 443, 445, 460, 461, 476, 477, 539,

754–757, 766

Monti S, 758Moran BT, 736Morell DB, 441, 442, 456, 461, 754Moroi Y, 598, 772Morris MD, 772Morse HN, 188Moscowitz AJ, 443, 452, 459, 470, 471, 497,

533, 539, 604, 755, 756, 761, 762, 766Mostovnikov GR, 769Mostovnikov VA, 769Mugnoli A, 445, 587, 754Mukerjee P, 597–599, 771–773Mulder GJ, 66, 196, 739, 743Müller F von, 24, 263, 364Müller N, 447, 478, 484, 749, 755, 758, 768, 771Muller P, 775Murakami Y, 760Murchison C, 68, 71, 73, 78, 92

NNagai Y, 760Nah JW, 760Nakanishi K, 474, 499, 501, 757, 761Nakayama Y, 773Naparstek A, 756Napoléon Bonaparte, 19Navon G, 461, 462, 464, 477, 591–593, 615,

755–757Nef JU, 216, 745Nencki WM, 179, 182–186, 189, 193–206,

209, 217–233, 236–244, 256, 264, 267, 268, 277–282, 292, 353, 525, 661, 662, 665, 667–669, 743–746

Neufingerl E, 758, 767Neuhaus D, 755Neukomm J, 69, 72, 78–83, 94, 105, 110, 740Neumann FW, 752Newman MS, 756Nichol AW, 441, 442, 456, 461, 754, 765Nicholson DC, 440, 441, 753, 757, 772Nicolaus RA, 753Niemann G, 310, 312, 401, 405, 693, 717,

724, 725, 732, 749, 750Nikitin EN, 611, 774Nogales DF, 463, 583, 607, 757, 758, 760,

770, 774Nolte RJM, 759Norona W, 770

OO’Carra, P, 443Ochi M, 769

Author Index 785

Odell GB, 754, 765, 766Ogawa J, 765Ogawa Y, 765Ogino T, 768ÓhEocha C, 440, 441, 451, 753, 755Okamoto Y, 760Okamura T, 773Olah GA, 343, 751Oldham-Tipton A, 608Onishi S, 533, 537, 543, 556–558, 567, 572,

574, 575, 765–769Onoda A, 773Orndorff WR, 182, 252, 743Orth H, 1, 264, 390, 402, 403, 429, 430, 735,

749, 752Ostrow JD 443, 452, 529–537, 540–558, 573,

587, 594–599, 603, 753, 764–767, 771–773

Ostwald W, 5, 19, 184, 212Overbeek JTG, 594–599, 602, 603, 772Overhauser A, 755Owens D, 443

PPaal C, 250, 747Palma LA, 555, 764, 766–770, 774Palyi G, 760Panigel R, 757Paologgi F, 772Papendieck A, 333, 334, 339, 340, 705,

708, 750Paracelsus, 3, 9, 11Park YT, 546, 767Parker G, 215, 669, 745Parks JS, 773Parris K, 773Partington JF, 736, 738Paton JD, 758Paul BD, 776Pavlov IP, 183Pederson AO, 767Pelletier PJ, 38, 738Pelloni RR, 474, 457, 755, 756Penfield SL, 745Pèpe G, 754Perrin H, 759Perrin JB, 5Perryman PW, 764Person RV, 481, 483–487, 506, 605, 758,

761, 774Peterson BR, 506, 758Petit AT, 112Petrarca AE, 755

Pettenkofer MJ von, 71, 78–80, 638, 639, 739Petterson KA, 773Pfeiffer P, 353, 751Pfeiffer WP, 488, 607, 774, 775Pflüger EWF, 740Philippus Aureolus Theophrastus Bombastus

von Hohenheim (Paracelsus), 3, 9, 11Phimister A, 773Piloty O, 182, 233, 236–294, 300–303, 306,

307, 334, 342, 353, 621, 675, 676, 682–689, 692, 705, 746, 747

Pimentel GC, 753Pirkle WH, 496, 760Pirone C, 775Pis Diez R, 774Pitea D, 477, 758Plancher G, 230, 677, 746Platner EA, 41, 42, 48, 49, 631, 632, 738Plaveskeiĭ VY, 769Plieninger H, 391, 412, 730, 731, 735, 752,

753, 761, 762Podobruk M, 772Poggendorff JC, 745Polonski T, 497, 760, 772Postowsky JJ, 313, 314, 401, 750Poulletier de la Salle, FPL 13, 14, 21Povalarapu P, 761Powers TW, 756Prakash GKS, 751Pratesi R, 488, 758, 769Pratt DC, 452, 755, 766Pregl F, 4, 19, 315Preuss I, 762Preyer WT, 85, 740Priestap HA, 775Priestley J, 9Pu YM, 614, 758–761, 763Puikynĕ JE, 57Pützer B, 750Puzicha G, 514, 613, 614, 758, 761, 774

QQuirke JME, 775Quistad GB, 412, 536, 752, 754, 765Quitmann E, 241, 244, 245, 277–279, 283,

675, 685, 746

RRadcliffe CB, 740Ramberg PJ, 182Rambert PJ, 743Ramonas L, 767

Author Index786

Randall EW, 755Ranking WH, 740Rao M, 755, 776Raoult FM, 182, 183, 185, 186, 239, 661,

662, 743Rapoport H, 744Rast K, 185, 695, 743Ratzenhofer M, 768Rawls HR, 761Rebek, 496, 601Rebek J Jr, 760, 771, 773Reichert ET, 195, 743Reichert KE, 195, 743Reindel F, 87Reinecke H, 398, 727, 752Reinhardt B, 738Reisinger M, 759, 760, 766, 769Remarque EM, 236, 746Renouard PV, 736Rhodes IP, 744Rhodes W, 761Ribó JM, 758, 771Ricca GS, 443, 460Rich AR, 87, 89, 740Richards DH, 764Richter V von, 745Richters VEM, 759Rimington C, 755Rinsler MG, 742Ritter SK, 756Roberts JD, 773Robin, CP, 62, 65, 66, 91, 640, 645, 739Rochleder DR, 738Rocke AJ, 182, 740Rödeler, 170, 660Rodríguez M, 763Rohmer T, 757Rokitansky, C, 62Roos, WT, 552, 574, 767Roscoe H, 112, 742Röse H, 46, 258–260, 262, 263, 268, 269, 271,

272, 283, 285–287, 294, 309, 400, 402, 410, 435, 681–684, 689, 693, 694, 724, 732, 748, 749

Rosenbach OEF, 16Rosenberg B, 478, 761Rosenberg H, 758Rosenfeld L, 736Rotschy A, 182, 184–186, 189, 661, 743Rubaltelli FF, 766, 767Rubires R, 771Rüdiger W, 1, 412, 443, 735Rumajntzev EV, 735Runge FF, 198, 250, 744

Ruppert J, 762Rush JE, 755

SSaalwächter K, 757Sahavattanapong P, 760Saleh M, 776Salek A, 761Salisbury J, 775Salkowski EL, 85, 86, 740Salzameda NT, 586, 771Sanders RH, 753Saresberiensis I, 775Saski K, 769Saunders M, 751Saunders W, 62, 739Saxton RG, 443Schaad LJ, 771Schaffer R, 754, 765, 766Schaffner K, 771Scheele CW, 9, 216Scheer H, 427, 621, 752, 753, 776Schellman JA, 467, 471, 757Scherer JJ, 41, 44, 45, 48, 49, 52–54, 56, 62,

63, 75, 94, 108, 114, 145, 175, 631–633, 637, 656, 738

Scheyer H, 321, 750Schindler H, 739Schlack P, 353–355, 750Schlederer T, 755, 768, 771Schmid R, 426, 528, 529–532, 619, 764,

770, 775Schmidt J, 746Schneller K, 750Schlögl K, 310Scholtan N, 467, 757Schønheyder F, 767Schönhofer A, 774Schönlein JL, 67Schubert M, 317, 750Schumm O, 338, 339–342, 708, 709, 750, 751Schwanert H, 199, 744Schwartz S, 601, 757Schwarz B, 774Scriver CR, 763Sedlak TW, 776Seidel W, 728Seidman DS, 763Senac JB, 67, 636Senge MO, 741Severini-Ricca GS, 755, 756Shapovalenko EP, 595, 772Sheldrick GM, 754

Author Index 787

Sheldrick WS, 444, 453, 754Shelver WH, 478, 484, 758Shelver WL, 758Shemin D, 528Showacre J, 766Shrout DP, 605, 760, 772, 774Sicherer HV, 196, 638Sieber N, 183, 196–204, 219, 238,

665, 744Siedel W, 1, 380, 386, 387, 395, 731, 735,

751, 752Silfen J, 756Simon JF, 41, 43, 44, 46, 47, 49, 50, 52, 63,

110, 135, 631, 738Simopoulos AP, 754, 765, 766Simpson, 216Skewes G, 756Sly WS, 763Small DM, 773Smith H, 426Smith KM, 517, 762, 774Snapper I, 775Snatzke, G, 514Snir J, 756Snyder SH, 755, 776Sommer U, 762Soper AK, 774Sorensen OW, 755Sorrenti A, 760Spielman PE, 745Spiess HW, 757Städeler GKA, 46, 49, 67, 68, 72–78, 91–120,

125, 126, 130, 136, 140, 143, 149, 160, 165–167, 177–179, 181, 184–186, 189, 190, 191, 195, 200, 203, 620, 621, 649, 650, 654, 658, 661–663, 665, 740

Stangler G, 389, 751Steinheil CA von, 149Steinmetz H, 326, 347, 369, 713, 717Steinsträsser R, 762Stern AJC, 264, 307, 357, 423, 429, 430, 470,

731, 735, 749, 757Stevenson DK, 763Stewart JCM, 443, 537, 765Stock J, 288, 689, 747Stocker R, 776Stokvis BJ, 158Stoll A, 748Stoll MS, 443, 553, 556–558, 567, 573, 574,

752, 767, 768Strecker A, 10, 42, 738Strope ER, 752Sugiyama S, 767, 768Sund H, 769

TTakeda J, 773Talafant E, 619, 775Tapia A, 762Taylor ER, 84, 740Teeple JE, 179, 182, 187, 252, 743Teichmann LK, 195, 197, 644, 663, 743Tenhuenen R, 443Thaler MM, 764, 768Thannhauser SJ, 252, 257, 260, 273, 282,

682–684, 746Thenard LJ, 4, 18, 20–27, 29, 30, 32–37, 39,

41, 44, 51, 114, 175, 624–628, 737Thiessen H, 595, 772Thirring K, 444, 754, 755, 768Thomson T, 21, 41, 736Thomson W, 736, 738Thudichum JLW, 49, 85, 86, 90, 91, 93, 110,

113–133, 140–149, 155–179, 181–185, 190–196, 203, 211, 225, 265, 342, 402, 406, 525, 534, 560, 655, 658, 659, 665, 672, 738, 740–742

Thyrann T, 605, 774Tiedemann F, 15–17, 24, 30–32, 41, 47, 136,

175, 619, 626, 736Tipton AK, 770, 771Tiribelli C, 599, 771–773Tissot G, 214–216, 226, 745Todd A, 444Tokumara K, 772Toledo LM, 771Tolstoy PM, 772Toyota S, 768Trallianus A (Alexander of Tralles), 50Treibs A, 337, 338, 363, 364, 414, 428, 430,

709, 735, 748, 751, 752Tret’yahova AI, 769Troup GJ, 769Troxler R, 443Trueblood KN, 756, 761Trull FR, 560, 604, 758, 760, 763, 768,

772–774Truscott TG, 769Tsai L, 756Tsoucaris G, 759Tsujino N, 759Tu B, 606, 612, 770, 774Turner E, 492, 736, 738, 759

UUeyama N, 601, 773Urbanová M, 497, 761Urey H, 392

Author Index788

VVaisman II, 774Valasinas A, 762Valentiner W (Valentin GG), 57–62, 66, 69,

72–74, 85, 86, 91, 94, 105, 106, 133, 175, 633, 634, 637, 644, 739

Valle D, 763Vallisneri A, 13, 51, 736van den Bergh H, 253, 439, 618, 619, 775van der Eijke JM, 759van der Steen R, 768van Goudoever, 196van’t Hoff JH, 11Vandemark FL, 766Varentrapp F, 4Vauquelin LN, 14, 20Vega-Hissi EG, 774Vicker N, 573, 768Vicq D’Azur F, 14Villani C, 760Vink CLJ, 595, 772Virchow RLK, 41, 45, 46, 58, 60, 61, 63, 64,

71, 73, 74, 84, 86–88, 150, 172, 175, 176, 634, 637, 738–740

Vogel FWC, 740Voit E, 745Voit C von, 10Volhard J, 251Voltaire (François-Marie Arouet), 10Vormayr G, 758

WWackenroder H, 48, 54, 739Wagner E, 85, 740Wagner R, 39, 41, 67Wagnière G, 475, 501, 757Walach B, 750Walden P, 212Wallace R, 57Wang CQ, 741, 751, 752Warren JC, 740Wash PL, 771Watchko JF, 763Watson CJ, 23, 24, 100, 144, 363–365, 433,

440, 443, 451, 470, 528, 533, 559, 604, 737, 751, 753, 757, 762

Watson GB, 559Watters K, 773Watts H, 742Webster CC, 598, 772Wedl C, 62, 64, 739

Weibel MH, 457, 474, 755, 756Weidel H, 250, 747Weiger HH, 767Weimer M, 753Weinland EF, 264Weissbarth O, 412, 418, 421–423, 730, 735Welch W, 773Weller JP, 762Wellman KM, 761Weltzien K, 112Wennberg RP, 545, 759Werner A, 353Westerdorf W, 736Wheen AW, 237Wieger HH, 552Wieland H, 264, 307, 428, 730, 748Wijekoon WMD, 493, 759, 760Wilen SH, 760Wilke K, 747Will H, 4, 747Williamson AW, 10, 112, 121, 181Williamson MP, 755Willstätter RM, 5, 6, 194, 235, 257, 262, 264,

275, 276, 281, 282, 298–300, 330–333, 336, 338, 349, 353, 354, 357, 359, 363, 429, 560, 680, 688, 690–693, 697, 698, 705, 732, 736, 748, 751

Wilsey M, 759Windler SCH, 552, 767Winkler L, 4Winsauer K, 768Winstein S, 174, 214, 342Wislicenus J, 46, 193, 251With TK, 441, 451, 753Wittig G, 343Wöhler F, 19, 29, 67, 71, 72, 75, 149, 173,

212, 552, 737, 745Wolf S, 773Wolkoff AW, 763Wollaston WH, 112Wolschann P, 771Wood ES, 740Woodward RB, 5, 444Woody RW, 756, 761Wooldridge TA, 547, 549, 765–767Woolley PV III, 472, 757, 759Wuest JD, 582, 583, 771Wurtz, 213

XXie M, 606, 770

Author Index 789

YYaffe SJ, 594, 772Yamada Y, 773Yamakawa T, 766, 768, 769Yamamoto H, 773Yamamoto Y, 776Yan F, 741, 751, 752Yashima E, 760Yasuoka H, 759Yokoyama T, 768Yonger J, 772Yoshiyasu K, 759

ZZabriskie J, 764Zaleski J, 219, 221–224, 228, 230, 231, 233,

236, 239, 244, 256, 277, 281, 282, 353, 745, 746

Zao KH, 776Zarembo JE, 764, 765, 767Zechmeister L, 1, 380Zeile K, 317, 353, 355, 428, 430,

748, 751Zelinsky N, 217, 745Zenker R, 73Zenone EA, 556, 557, 767Zhang MH, 759, 760Zhou M, 621, 776Zhu XX, 757Zietz B, 769Zincke T, 239Zrunek U, 755Zucchi C, 760Zumbusch LR von, 190, 743Zunszain PA, 769Zuntz N, 171Zwicky F, 62

791D.A. Lightner, Bilirubin: Jekyll and Hyde Pigment of Life, Progress in the Chemistry of Organic Natural Products, Vol. 98, DOI 10.1007/978-3-7091-1637-1, © Springer-Verlag Wien 2013

AAcetoacetic ester, 216N-Acetyl-2-hydroxypyrrole, 440Acidum cholonicium, 36Acidum fellicum, 36Acyl glucuronides, 253, 617Adipocire, 14, 21Albumin, 23, 164, 173, 458, 488, 568, 621,

625, 628, 632, 733Heller’s ring test, 173

AM1 computations, 479Amide-amide hydrogen bonding, 581Amide-carboxylic acid hydrogen bonding, 581(S)-2-Aminobutane, 490, 493Aminoethyl-dipyrrinone, 419Ammonia, 4, 32, 97, 99–105, 116, 154, 227,

620, 624, 627, 657, 662, 688Ammonium cholate, 79, 80Ammonium cyanate, 20Ammonium hexachloroplatinate, 654Ammonium hydroxide, 25, 51–53, 540, 549,

641, 667Antioxidants, 622Asymmetric transformation, first-order, 490,

492, 501Atomic weights, 5, 28, 89, 111, 121, 198, 342

BBacteriochlorophyll, 5Baryta water, 36, 37, 626–629Beckmann thermometer, 184Beer-Lambert law, 153, 154Benzenediazonium chloride, 87Bile, 7Bile acids, 28, 35, 42, 82, 625, 637–640,

644, 645

Bile pigments, 43, 45, 47, 50, 86, 94, 108, 173, 235, 354, 465, 506, 525, 604, 620, 624, 645, 655–667, 694, 698, 729–731

Bile pigments, absorption spectra, 657chemical behavior, 631cleavage, 294computational studies, 477separation, 115spectroscopy, 149, 155, 506, 533synthesis, 517

Bile, bilirubin-biliverdin separation, 28Biliflavin, 128Bilifulvin, 37, 39, 48, 49, 58, 62, 73, 84, 629,

631, 635, 637, 643Bilifuscin, 95, 100–105, 110, 111, 125, 155,

643, 649, 658Bilihumin, 95, 102–105, 110, 111, 125, 649Bilin, 44Bilinic acid, 252–254, 257–259, 268, 375Biliphäin, 43, 44, 46, 47, 49, 52–56, 58,

60–63, 67, 101, 133Biliprasin, 95, 101–105, 108, 110, 111, 125,

136, 649, 658Bilipurpurin, 128Bilirubin, albumin bound, 458

chelates with transition metals, 458chemical structure, 182Cholepyrrhin, 40cleavage, 264composition/formula (Heintz), 177conformational dynamics by NMR, 475degradation products, 535diglucuronide, 617, 618dimethyl ester, 727double bond stereochemistry, 450(E)-configuration isomers, 545

Subject Index

Subject Index792

Bilirubin, albumin bound (cont.)elemental combustion analyses, 187exciton chirality CD spectra, 506exo-vinyl group, 408Gallenroth, 93–95kaput, 317molecular exciton, 497molecular fragmentation, 193NMR, 442optical activity, 488Piloty, 238solubility, 590structure, 5, 309, 354, 398, 412SYBYL molecular dynamics

calculations, 480synthesis, 363, 398, 412(Z,E) diastereoisomers, 526IIIα, 405, 400, 539, 557, 561–565, 570, 571IXα, 451, 578, 729

synthesis, 420, 421(Z/E) diastereoisomers, 448

XIIIα, 405dimethyl ester, 411

Bilirubin-albumin CD Cotton effects, 498Bilirubin-HSA complex, 470Bilirubinic acid, 259, 268, 274, 276, 295, 309,

324, 358, 367, 435, 693isomers, 371

Bilirubinuria, 72Bilis, 36

bubula spissata, 27Biliverdate salt, 131Biliverdin, 5, 37, 40, 49, 88, 100, 406,

629–668, amide, 134conversion to bilirubin, 729dimethyl ester, 445synthesis, 391, 730, 731IXα, 421, 729

dimethyl ester, 419, 421, 424, 453XIIIα dimethyl ester, 417–419, 427

Biliverdin-chlorophyll correlation (Berzelius), 39

Biliverdinamid (biliverdin amide), 134Biliverdinsäure (hematinic acid imide), 207,

209, 225, 668Biliviolins, 406Bilixanthin, 172Bird of Paradise plant (Strelitzia reginae), 621Bis(2,4-dimethyl-3-carbethoxy-5-pyrryl)

methene, 697Bis(3-ethyl-4-methyl-5-carbethoxy-2-pyrryl)

methane, 322Bis(3-propionic acid-4-methyl-5-carboxy-

pyrryl)-methane, 343

Bis(aminoethyl)verdin, 417Bisdipyrrylmethene, 322Bishydroxypyrrole, 440Bis-isopropylammonium salt, 445Bis-lactam, 444Bis-lactim, 443

methyl ether, 446Blattgrün (chlorophyll), 40Body fluids, 3Bone oil, 252Bovine serum albumin (BSA), 458, 468, 541,

549, 573Brownian motion, 5Bunsen-Kirchhoff scale, 153, 154Bunsen-Kirchhoff-von Steinheil

spectroscope, 154(2-Butenyl)benzene, 213

CCannizzaro reaction, 362, 716Carbon–carbon double bonds, exocyclic, 434Carboxyl carbon–dipyrrinone, N-hydrogen

distances, 463Carboxylic acid–carboxylic acid, hydrogen

bonding, 581Caustic ammonia (NH4OH), 32, 33Caustic potash (KOH), 33Chirality, 467, 475, 488, 575, 604Chlorophyll, 5, 6, 38–40, 42, 43, 48, 63, 182,

221, 235, 262, 276, 281, 282, 298, 303, 308, 337, 353, 357, 363, 380, 388, 408, 428, 429, 433, 604, 620, 629, 635, 720, 732

synthesis, 363Cholaric acid, 44Choleic acid (Choleinsäure), 28, 625Cholephäin, 50, 645, 646Cholephäinate (Sesquicholiphäinat), 123–126,

646–649Cholepyrrhin, 40, 41, 43, 46, 47, 49, 53–56,

58, 60–63, 84, 91, 110, 133, 630, 631, 634, 652–657

Cholerythrine, 115, 118, 119, 645Cholesterol, 11, 13, 26, 28, 51, 58, 62, 94,

106, 117, 135, 186, 433, 628, 633, 644

Choletelin, 166Cholethalline, 156Choleverdin, 158Cholic acid, 28, 30, 37, 41, 76, 79, 80, 109,

625, 628, 639Cholinsäure, 36Cholochloine, 114, 116, 127Cholochrome, 114, 116

Subject Index 793

Cholochromic acid, 116Cholidinic acid (Choloidinsäure), 28, 625Choloidic acid, 639Cholophæine (= Cholepyrrhin = Biliphäin),

114–122, 126, 130Cholsäure, (cholic acid), 28, 30Chromogen, 70Circular dichroism (CD), 457, 467, 472, 488,

490, 492Citraconimide, 230, 244Citric acid, 213Claisen condensation, 216CNDO/2 molecular orbital calculation, 477Color diagnostics, 15Colorimetry, 149Combustion analyses, 11, 17, 30, 49, 50, 56,

65, 89, 187, 633, 714, 729quantitative, 17

Combustion train (Kaliapparat), 18Conformational dynamics, 477Conformational energy maps, 484Conjecturalchemie (conjectural chemistry),

162, 170, 525, 560Contour map, 482Coproporphyrin, 326, 339, 344, 702, 708–713Corey-Pauling-Koltun space-filled molecular

models, 459, 473Cotton effect, 458, 469, 472, 491, 505, 510,

514, 519, 522, 615Curtius’ rearrangement, 414Cyanobacteriochromes, 621Cyclobilirubin, 575Cyclodextrins, 489, 493, 495, 497Cytochrome, 5

DDehydrobilinic acid, 257–261, 269Dehydrobilirubin, 390Dehydrochloridhämin, 232Diazo reactivity, visible light, 529Diazonium salts, 618Diazotized sulfanilic acid, 253α,α′-Dibromodipyrrylmethene, 322, 328, 343,

346, 350Diethyl ethylmalonate, 217Diethylmaleimide, 227, 230, 242, 673Diethylmalonate alkylations, 217Dihalogen-hematoporphyrin-dimethyl

ether, 335Dihydrobilirubin, 393, 724, 725

IIIα, 405Dihydrofuran, 405, 721, 723, 725Dihydromesobilirubin, 394

XIIIα, 405

Dihydropyrrole, 691Di-isopropylammonium bilirubinate, 454

chloroform solvate complex, 4452,4-Dimethyl-3-acetylpyrrole, 279, 3182,4-Dimethyl-3-carbethoxy-pyrrole, 317, 6972,4-Dimethyl-3,5-diethylpyrrole, 2792,3-Dimethyl-5-ethyl-4-propionyl-pyrrole, 2912,3-Dimethyl-4-ethylpyrrole, 282, 283, 6852,4-Dimethyl-3-ethylpyrrole, 279, 282, 674,

678, 6852,3-Dimethyl-5-ethylpyrrole, 2902,4-Dimethyl-5-ethylpyrrole, 280, 284p-Dimethylaminobenzaldehyde, 253, 267,

681, 720Dimethylmaleic anhydride, 214, 226Dimethylmesobilirubin-XIIIα, 516Dimethylpyrrole, 230, 244, 249–252, 271,

280, 679, 684, 6862,3-Dimethylpyrrole-5-acetic acid, 284, 687α,β-Dimethyl-β-ethylpyrrole, 232, 243,

277, 2782,3-Dimethylpyrrole-4-propionic acid, 2882,3-Dimethylpyrrole-5-propionic acid,

284, 687α,β-Dimethyl-β-pyrryl-propionic acid, 244, Dinitrotyrosine, 91Dippel’s oil, 250Di(propionic) acids, 311Dipyrrinone-carboxylic acid hydrogen

bonding, 580Dipyrrinone-dipyrrinone dimers, hydrogen-

bonded, 584Dipyrrinone-urethane, 416Dipyrrinones, 376, 414–416Dipyrroles, 296, 358, 367, 371, 380–385,

439, 600synthetic, 371

Dipyrrolic halves, 333Dipyrrylmethanes, 260, 314, 701Dipyrrylmethenes, 260, 262, 298, 318, 324,

334, 384brominated, 326, 328, 346CNDO/2, 477dibrominated, 321

Dipyrryl-pyridyl-methane, 307Dipyrryl-pyrryl-pyridyl-methene, 305Double bonds, exocyclic, 448Dyslysin, 36

EEhrlich reaction, 360Energy hypersurface, 482Erythrosin, 91Ethyl acetoacetate, 215, 216

Subject Index794

Ethyl α-bromopropionate, 217(endo-Ethyl, endo-ethyl)-mesobilirubin, 378(exo-Ethyl, exo-ethyl)-mesobilirubin, 378(exo-Ethyl)iso-neoxanthobilirubinic acid, 404Ethylitaconic acid = propylidene-succinic

acid, 213Ethylmesaconic acid, 2128- Ethylmesobiliverdin-XIIIα, 6003-Ethyl-4-methyl-5-bromo-2-formylpyrrole,

3843-Ethyl-4-methyl-5-carboxyl-2-formylpyrrole,

384(S)-Ethylmethylsulfoxide, 497(endo-Ethyl)neo-xanthobilirubinic acid, 405Ethylparaconic acid, 213endo-Ethyl xanthobilirubinic acid, 387exo-Ethyl xanthobilirubinic acid, 385Etiobilirubin, 317, 483Etiobilirubin-IVg, potential energy

hypersurface, 483, 484Etiomesobiliverdin-XIIIα, 453Etioporphyrin, 298, 300, 319, 345, 346, 349,

354, 691, 700Etioporphyrin, isomers, 347Etiophyllin, 691Exciton chirality, 497Exocyclic double bonds, 448

FFarbstoff, 30, 32Fellinic acid (Fellinsäure from Fel fellis,

bile), 36, 44Fleischextract (meat extract), 30Furans, 251, 312–317, 354, 403, 552Furano-pyrrole, 401

GGalactaric acid, 199Gallenbraun, 46, 47, 49, 52–56, 63, 77, 103,

118, 119, 175, 620, 631, 633Gallenfarbstoff (bile pigment), 43, 45, 47, 52Gallenfett (Cholesterin cholesterol), 28, 626Gallengrün, 38, 43, 47, 49, 56, 110, 631Gallenharz (bile resin), 26, 30, 625, 628Gallenroth, 93–95, 110, 620, 640Gallensäure (Acidum cholicum, Cholsäure) or

cholic acid, 30Gallenspäragin, 30Gallenstoff, 23, 26, 626Gallenzucker, 26, 30, 31, 36, 37, 625, 628Gallstones, 10-14, 19–90, 93–156, 175, 187, 191,

206, 224, 235, 265, 539, 618, 620

bile pigments, 50, 235, 539, 620classification, 116fat, 14

Glaucobilin, 390Gliadin, 30Global energy, 483Glucuronidation, 530Glucuronides, 50, 253, 455, 529, 557,

605–609, 617, 619Glucuronosyl transferase, 530Glycine, 77Glycocholic acid, 76, 77, 80, 637Gmelin reaction, 25, 42, 84, 98, 102, 104, 108,

110, 142, 147, 158, 175, 182, 360, 362, 368, 379, 390, 393, 421, 530, 715–718, 721, 722

HHämatin (hematin), 46, 58, 65, 182, 195Hämatoidin, see, hematoidinHämatolin, 195, 198Hämatopyrrolidinsäure, 263Hämatosin (= Hämatin), 65Hämin, see, heminHämopyrrol, 217, 221–223Hämopyrrolcarbonsäure, 283Hämotricarbonsäure, 226Harnfarbstoff (urea), 45Hematin, 46, 58, 65, 83, 195, 201, 204,

635–637, 640, 662–669Hematinic acid, 204, 207, 228, 254, 266, 283,

295, 300, 334, 666–676, 680, 683, 689, 706, 725

dibasic, 217imide, 228, 233, 235, 242, 243

Hematoidin, 58, 60, 62, 64, 67, 85, 91, 182, 633–637, 640, 644, 645, 664, 698

Hematoporphyrin, 87,183, 194, 196, 201, 222, 267, 278, 283, 332

Hematopyrrolidinic acid, 239, 241, 244, 254, 260Heme, 5, 71, 78, 449, 465, 466, 560Heme oxygenase, 71Hemibilirubin, 259, 266, 270, 297, 682–685Hemin, 5, 182, 195, 200, 235, 307, 354, 357,

367, 371, 381, 449, 525, 603, 621, 697, 704

dimethyl ester, 706ester, oxidative cleavage, 331structure, 299–302tetrapyrrylethylene-based, 317unsaturated β-substituents, 338

Hemoglobin, 63, 71, 78, 88, 94, 183, 193–196, 206, 334, 337, 707

Subject Index 795

Hemopyrrole, 281, 288, 294, 673, 688, 689, 720

carboxylic acid, 239, 240, 244, 255, 283, 293, 294, 366, 687, 710, 711

Hexachloroplatinate method, 45Hexahelicene, 459, 471Hexahydrohematoporphyrin, 198, 663Hofmann elimination, 414, 420Human serum albumin (HSA), 468, 472, 489,

495, 530, 557, 570, 576, 615Humin, 100Hydrazide, 414Hydrobilirubin, 144, 154, 159, 161, 162, 172,

185, 196Hydrofuran, 406, 410Hydrogen bonding, 434, 442–445, 455,

482–522, 528, 533, 543–553, 575–614, 621

misconceptions, 587intramolecular, 594

Hydroxydipyrrylmethene, 733Hydroxypyrrole, 309, 440, 443

tautomer, 439lactim, 310

α-Hydroxypyrromethenes, 438, 451Hyperbilirubinemia, 526

IIcteric urine, 56, 67, 73, 74, 80, 90, 103, 108,

118, 633, 637–639Indican, 173Indigoblau (indigo blue), 173, 624, 637, 642Indigogen, 173Indirubin, 173, 661Indole, 199, 250, 663, 677Infrared (IR), 434, 439–442, 552, 554, 574Intramolecularly hydrogen-bonded

conformation, 496Isohemopyrrole, 281, 293, 294Isoindole, 242, 243Isolumirubins, 568Isomeric phonopyrrole carboxylic acid, 259,

273, 285, 292Iso-neo-bilirubinic acid, 399, 718Iso-neo-xanthobilirubinic acid, 383, 385, 398,

438, 718–720, 725methyl ester, 399

Isophonopyrrole carboxylic acid, 255, 256, 259, 268, 273, 285, 293, 684, 687, 689

Isopropylamine, 492Isopyrrole lactim, 435Iso-xanthobilirubinic acid, 375, 383Iso-ψ-xanthobilirubinic acid, 375

JJaundice (icterus), 2, 23, 33, 44, 64, 67, 71,

97, 176, 489, 522, 526, 574, 618, 627–630

neonatal, phototherapy, 97, 526, 527, 544, 548, 550, 604

KK-mesobilirubin, 368, 370, 375, 380

dimethyl ester, 369K-mesobilirubinogen, 369Käsestoff (cheesy material), 30Kernicterus, 526, 529Kryptopyrrole, 274, 282, 283, 293, 294, 296,

322, 358, 688, 689, 694, 712, 714carboxylic acid, 293, 294, 296, 324, 358,

366, 701, 710, 714Kryptopyrrolenone, 393Küster’s maleimides, 217Küster-Fischer polemics, 329

LLactam, 305, 309, 435, 563, 733Lactam-hydroxypyrrole, 355Lactic acid, 216Lactim, 305, 309, 435, 461, 528, 563, 733Lactim-lactam tautomerism, 435, 563Lactose, 199Lead oxide, 20Leucine, 76Lumirubins, 568Lutein (xanthophyll), 85

MMaleic acid, 212, 216, 668, 672, 675

imide, 673, 674, 677Maleic anhydride, 215Malonic acid, 217Margaric acid (Margarinsäure), 30, 626, 628Matière jaune de la bile, 34, 39Meconium (cholesterol, picromel, etc.), 43Melanin, 105, 643Melting points, discordant, resolution, 379Mesobilirhodin, 440Mesobilirubin, 24, 296, 303–305, 310, 311,

369–440, 444–523, 561–614IIIα, 382, 385, 396–398, 405, 722IVα, 495IXα, 382, 389, 392, 395–398, 437, 454,

570, 722dimethyl ester, 496

Subject Index796

Mesobilirubin (cont.)synthesis, 392

XIIIα, 382, 385, 396, 400, 405, 437, 463, 480, 506–513, 517, 522, 561–566, 570, 580, 584, 587, 592, 600, 604–614, 722, 726

dimethyl ester, 496, 694dipyrrole fragments, 365synthesis, 379

Mesobilirubinogen, 24, 297, 303–305, 360, 369, 695

Mesobiliverdin, 440IXα (glaucobilin), 390XIIIα, 600

Mesobiliviolin, 24, 440Mesohemin, 311, 381–383

XIII, 383Mesoporphyrin, 87, 223, 224, 230, 272, 297,

323–326, 329–332, 347–354, 362, 671, 685, 700, 704, 705, 713–716

isomers, 347synthesis, 713IX, 351

Mesoporphyrinogen, 325Methemoglobin, 707β,β′-Methyl-äthyl-pyrrol, 232β,β′-Methyl-äthyl-pyrrolin, 232Methyl ethyl maleic acid, 212

anhydride, 2123-Methyl-4-ethylpyrrole = Opsopyrrol =

opsopyrrole, 414Methylethylmaleic anhydride, 214, 217,

228, 229Methylethylmaleimide, 216, 228, 243, 254,

267, 269, 277, 295, 359, 412, 696Methylethylsuccinic anhydride, 214, 2152-Methylhexandisäure-3-methylsäure, 226Methyl isobutyl ketone (MIC), 733Methylisopropylmaleimide, 2273-Methyl-2-(2-methylpropanoic acid)

pyrrole, 283Methyl-n-propylmaleic acid, 226

anhydride, 226Methylpropylmaleimide, 227, 231, 241, 243Methylpropylpyrrole, 222, 231, 241, 243, 277N-Methylpyrrole, 200, 6794-Methylpyrrole-3-propanoic acid, 266Methylsuccinic acid, 213, 214, 216, 669, 673Methylvinylmaleimide, 359, 408, 411,

537, 696(βS)-Methylxanthobilirubinic acid, 500Microanalysis, 19Molecular exciton, 497Molecular mechanics computations, 477

Molecular weight, 121, 183, 187Mono-oximes, 256, 685Monopyrrole propionic acid, 283Monopyrroles, cleavage of hemin, 294

Fischer, 366Mucic acid, 199, 200Mucus (Schleim), 12, 23, 30, 37, 44, 52, 62,

71, 624–630

NNencki’s Hämopyrrol, 217, 221, 226, 238Neo-bilirubinic acid, 366, 377Neo-xanthobilirubinic acid, 366, 378, 383,

384, 398, 400, 437, 718, 719, 733ester, 399, 719

Nitritkörper (nitrite body/nitrite compound), 400, 724, 726

Nuclear magnetic resonance (NMR), 434, 461, 475

13C, 4471H, 476

Nuclear Overhauser effect (NOE) nuclear magnetic resonance (NMR) spectroscopy, 452

OOctahydrobilirubin, 297Oleic acid (Oelsäure), 28, 30, 626, 628Omnicholin, 163, 172, 660Opsopyrrole, 384, 414, 727

carboxylic acid, 366, 414, 415, 418, 427, 728

ORD (optical rotatory dispersion) spectra, 458, 467

Osmazom, 303-Oximino-2-pentanone, 280

PPettenkofer test, 82Phenylparaconic acid, 213Phlogiston, 9Phonopyrrole, 246, 247, 278, 283, 290, 677,

678, 688carboxylic acid, 245, 256, 260, 283, 285,

290, 292, 293, 296, 676, 682–689Photobilirubins, 541, 547, 554–559, 567,

572–575, 593Photodegradation, 537Photoisomerization pathway, 556Photoisomers, 554Photolysis, 534, 545–547, 562, 567–573

Subject Index 797

Photo-oxygenation, 536Phototherapy, 97, 443, 522, 526–577, 604, 621Phycoerythrobilin, 440Phycorubins, 427, 621Phyllopyrrole, 274, 281, 282, 293, 295,

680, 686carboxylic acid (2,3,5-trimethylpyrrole-3-

propionic acid), 282, 295, 296, 366, 689

methyl ester, 287Picric acid, 248Picromel, 21, 30, 35–37, 43, 51, 625, 628Pigment separation, 20Pigments of life, 5PM3 computations, 479Polemics, 342Porphin, 323Porphyrinogen, 272Porphyrins, 323–364, 389, 449, 453, 517, 545,

560, 578, 671, 692, 730spectral analysis, 339, 697, 698synthesis, 337, 344

Porphyrinuria, 339Potential energy hypersurface, 483Propentdyopents, 536Propionic acids, 217, 347, 354, 460, 472, 677,

687–689, 705, 727Propylfumaric acid, 212Propylmaleic anhydride, 213Propylsuccinic acid, 212Protoporphyrin, 341, 352, 361, 370, 407, 413,

714–717IX, 352, 590

Pterobilin (= γ-bilirubin), 422Pyridone, hydrogen-bonded homo-dimers, 583Pyrrofuran, 407Pyrrol, 198, 219Pyrrole, 7, 198, 219, 413, 663, 676, 679

β-carbons, 329Pyrrole acid imine, 300Pyrrole 3-carbethoxy ester, 280Pyrrole carboxylic acids, 286, 309, 687Pyrrole picrate, 2802-Pyrrolenone tautomers, 439, 443, 3-Pyrrolenone tautomers, 310, Pyrrolidone ring, 446Pyrrolin, 232Pyrrolo-furan, 402Pyruvic acid, 214–216, 669, 672, 673

RResorcinol melt, 399Rubin dimethyl ester, 416

SSaligenin, 77Schumm-Fischer polemics, 338Self-dimerization, 325[6]-Semirubin, 586Singlet oxygen, 528Skatole, 247, 255, 677Sodium amalgam, 642, 656, 661, 662, 694,

696, 715, 724Sodium deoxycholate micelles, 495Sodium dithionite, 427, 731Sodium glycocholate, 76, 81, 637, 639Sodium hydrosulfite = sodium dithionite, 421,

423, 425, 729, 730Sodium methylsuccinate, 216Sodium taurocholate, 70, 76, 637, 638Soxhlet extractor, 140Spectrum analysis, 149Speichelstoff (ptyalin), 30Spermaciti, 14Spin-lattice carbon relaxation time, 461Spirobilirubin, 574Stercobilin, 440, 470, 497Strelitzia reginae, 621Succinic acid, 212, 213, 216, 225, 228,

229, 672Sulfuric acid, 35SYBYL forcefield, 478

TTartaric acid, 216, 662Taurine, 26, 28, 37, 41, 44, 70, 77, 625,

628, 630Taurocholic acid, 638, 645Tetra-(2,3-dimethyl-4-carbethoxy-pyrryl)-

ethylene, 697, 698Tetrahydrophthalic anhydride, 242Tetramethylindole, 251Tetrapyrroles, 2, 355, 678, 725, 731

synthetic, 371Tetrapyrrylethanes, 317, 318, 320, 697Tetrapyrrylethylene, 275, 306, 314,

319, 320, 327, 329, 361, 370, 715–717, 732

Tetrapyrrylmethene, 306Torsional degrees of freedom, 4812,3,5-Trimethyl-3-ethylpyrrole, 2812,3,5-Trimethyl-4-ethylpyrrole, 282Trimethylpyrrole, 248, 271, 284, 684, 6892,3,5-Trimethylpyrrole, 284, 293, 6892,4,5-Trimethylpyrrole, 281, 6862,3,5-Trimethylpyrrole-3-propionic acid, 2822,4,5-Trimethylpyrrole-3-propionic acid, 287

Subject Index798

Tripyrrylmethanes, 321Tyrosine, 74, 76, 78, 91–93, 638, 640

UUltraviolet-visible (UV) spectra, 491, 493Urea, 19, 20, 43, 44, 652Urerythrin, 159Urethane, 414, 415, 420, 728Urethane-dipyrrinone, 418, 420Urobilinogen, 23, 253Urobilins, 145, 154, 159, 163, 166, 265, 267,

360, 433, 440, 459, 470–473, 497, 539, 604, 656, 658, 660–667, 682, 715

Urochrome, 145, 159, 172Urohodin, 173, 661Uromelanin, 173Uropittin, 163Uroporphyrin, 339Urorhodin, 163Uroxanthin, 172, 660Uteroverdin, 390, 720

VVerdins, 417, 427, 441, 453, 731

reduction to rubins, sodium dithionite, 427

Verdin amide, 417Verdin bis-urethane, 420Verdin dimethyl ester, 416Vinyl-dipyrrinones, 400Vinyl-iso-neo-xanthobilirubinic acid, 409exo-Vinyl-iso-xanthobilirubinic acid, 409Vinyl-neo-xanthobilirubinic acid, 399, 409, 731endo-Vinyl-neo-xanthobilirubinic acid, 409

Vinyl-neo-xanthobilirubinic acid methyl ester, 411, 418

(endo-Vinyl) vinyl-neoxanthobilirubinic acid methyl ester, 419

Vitalism, 20

WWeighed quantities, 9Wurtz reaction, 213

XXanthobilirubinic acid, 260, 270, 274, 275,

276, 287, 295, 296, 298, 309, 358, 367, 371, 383, 434, 435, 499, 684, 693, 717–720

dimer, 584ester, 314methyl ester, bromination, 376

PES spectra, 446synthetic, 375

Xanthopyrrole carboxylic acid, 256, 270, 285, 293, 366

Xeronimide (diethylmaleimide), 227, 230, 242, 673

X-ray crystallography, 446, 453, 465, 479, 575, 579

X-ray photoelectron spectroscopy (PES), 446

YYellow “magma”, 23

ZZerevitinov determination, 314