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FLAVINSAND FLAVOPROTEINS
1999
PROCEEDINGS OF THE THIRTEENTH
INTERNATIONAL SYMPOSIUM
KONSTANZ, GERMANY, AUGUST 29 - SEPTEMBER 4, 1999
EDITORS
S. GHISLA • P. KRONECK
P. MACHEROUX • H. SUND
RUDOLF WEBER
AGENCY FOR SCIENTIFIC PUBLICATIONSBERLIN 1999
XV
Contents
I. General Aspects:History,Chemistry, Physics and Theory
Living through various phases of flavin research 3Helmut Beinert
Synthetic Models of flavoenzyme activity 17Vincent Rotello
NMR-studies of flavocytochrome b2 reconstituted with15N, I3C labelled flavinGarit Fleischmann, Franz Miiller, Heinz Riiterjans, Florence Lederer
One and two electron redox cycles in flavin-dependent dehydrations 31W. Buckel, I. Cinkaya, S. Dickert, U.Eikmanns, A. Gerhardt, M. Hans,M. Liesert, W. Tammer, A. J. Pierik, E. F. Pai
Dipole moments and polarizabilities of flavins explored usingStark-effect spectroscopy ' 41Robert J. Stanley, Haishan Jang
Flavin binding thermodynamics in Enterobacter cloacaenitroreductase 45Ronald L. Koder, Michael E. Rodgers, Anne-Frances Miller
Regulation of flavin functions by hydrogen bondings 49Yumihiko Yano, Takeshi Kajiki, Hideki Moriya
The hydrogen bonding in flavoproteinThe effect of hydrogen bonding of flavin (neutral semiquinone state) 53Yoshitaka Watanabe
Substituent effect on redox states, spin densities and hyperfinecouplings of free flavins and their 5-deaza analogues 59Ryszard Zielinski. Henryk Szymusiak
Theoretical destabilization of the flavin semiquinone of Enterobactercloacae nitroreductase by a hydrogen-bonding -bending mechanism 63Joseph D. Walsh, Anne-Frances Miller
XVI
Supramolecular models of flavoenzyme redox processes 67Catherine Mclntosh, Angelika Niemz, Vincent Rotello
Electronic effects of 7 and 8 ring substituents as predictors offlavin oxidation-reduction potentials 71Dale E. Edmondson, Sandro Ghisla
Autoxidation of photoreduced 3,4-dihydro-6.7-dimethyl-3-oxo-4-D-ribityl-2-quinoxalinecarboxamide, an analog of riboflavin,and identification of oxygenated intermediates 77K. Matsui, Y. Nishina, K. Sato, K. Shiga
Intermediate products of 1,5-dihydroflavins autoxidationon the basis of density functional theory studies 81Henryk Szymusiak, Ryszard Zielinski
II. Spectroscopy
Advanced EPR spectroscopic studies of mutants of ferredoxin-NADP+ reductase from pea 87Milagros Medina, Carlos Gomez-Moreno, Richard Cammack,Adrian K. Arakaki, Nestor Carillo, Eduardo A. Ceccarelli
Radical intermediates in Escherichia coli DNA photolyase:EPR and ENDOR studies 91Gerald Richter, Christopher W. M. Kay, K. Struck,Peter Sadewater, Klaus Mobius, Stefan Weber
Resonance Raman study on the interaction between Hog kidneyD-amino acid oxidase and substrate analogs 95Ruiwen Shi, Yasuzo Nishina, Kyosuke Sato, Kiyoshi Shiga, Retsu Miura
Direct measurements of ultrafast excited state quenching ofisoalloxazine by adenine in FAD 99Robert J. Stanley, Alexander W. MacFarlane IV
XVII
III. Flavins and Electrons
1. Electron-Transfer in Heme-containing Systems
Flavocytochrome c3: The structure and mechanism revealed 105S.K Chapman, C.A. Morrison, G.A. Reid, S.L. Pealing,P. Taylor, M.D. Walkinshaw
Two FCSD flavoproteins involved in sulfur metabolism and a thiosulfateutilization gene cluster from the green phototrophic bacterium,Chlorobium limicola (strain Tassajara) 115Fabienne Verte, Yves Guisez, Terrance E. Meyer, Michael A.CusanovichJozef J. Van Beeumen
A flavohemoprotein from the cellulolytic fungus Humicola insolvenscontains 6-hydroxy-FAD as the dominant active cofactor 119Kiyohiko Igarashi, Marc F. J. M. Verhagen, Masahiro Samejima,Martin Schiilein, Karl-Erik L. Erikson, Takeshi Nishino
Changing the heme ligands of flavocytochrome b2:site-directed mutagenesis of histidine 66 to cysteine 123Christopher G. Mowat, Stephen K. Chapman,Caroline S. Miles, Graeme A. Reid, A.W. Munro
Cloning and characterization of a membrane-bound flavocytochrome cfrom the purple phototrophic sulfur bacteriumEctothiorhodospira vacuolata 127Vesna Kostanjevecki, Yves Guisez, Terrance E. Meyer,Michael A. Cusanovich, Jozef J. Van Beeumen
Electron transfer from FAD to heme-Fe in plant NADH:nitrate reductase 131Jeffrey A. Mertens, Wilbur H. Campbell, Lawrie Skipper, David J. Lowe
Expression, purification and mutagenesis of flavocytochrome c-sulfidedehydrogenase from Chromatium rinosum 135Lina De Smet, Yves Guisez,Terrance E. Meyer, Michael A. Cusanovich,Jozef J. Van Beeumen
The active site base of the fumarate reductase fromShewanellaftigidimarina 139Mary K. Doherty, Stephen K. ChapmanCaroline S. Miles, Graeme A. Reid
XVIII
Molecular recognition in the flavin domain of flavocytochrome b2 143Ruth K. Moysey, F. Welsh, Stephen K. Chapman, S.L. Rivers,Graeme A. Reid
Key substrate binding residues in flavocytochrome P450 BM3 147T.W.B. Ost, M.A.Noble, S.K.Chapman, Caroline S. Miles, J. Murdoch,G.A. Reid, A.W. Munro
The flavoprotein domains of nitric oxide synthase isoforms:site of possible regulatory control of flavin to heme electron transfer 151R. Timothy Miller, Pavel Martasek, Jonathan S. Nishimura, Satya Panda,Dawn E. Harris, Linda J Roman, Bettie Sue Masters, Jung-Ja P. Kim
Analysis of the redox properties of the human diflavin enzyme NADPH-cytochrome P450 reductases and its domains 155Andrew W. Munro, T. McSorley, Michael A. Noble, Laura Robledo,Stephen K. Chapman
Crystallographic insights into the hydride transfer mechanism ofNADPH-cytochrome P450 oxidoreductase 159Paul A. Hubbard, Rosemary Paschke, Jung-Ja P. KimAnna L. Shen, Charles B. Kasper
Flavodoxin as module for transferring electrons to differentc-type and P450 cytochromes in artificial redox chains 163Sheila J. Sadeghi, Yergalem T. Meharenna and Gianfranco Gilardi
Mechanic studies on the one-electron reduction of quinonesby neuronal nitric-oxide reductase domain 167Hiroyuki Matsuda, Shigenobu Kimura and Takashi Iyanagi
Calmodulin activates intramolecular electron transfer betweenthe two flavins of neuronal nitric-oxide synthase reductase domain 171Hiroyuki Matsuda, Shigenobu Kimura, Takashi Iyanagi
2. Electron Transfer in Flavodoxins
The binding of FMN to Anabaena apoflavodoxin 175Anabel Lostao, Fatna Daoudi, J. Sancho
XIX
Egression of recombinantflavodoxin from M^gasp/wera elsdem;effects of mutating the residues (M57, W91) that sandwich thednnethylisoalloxazine of the bound FMN 179Mary E. Gallagher, Susan M. Geoghegan, Stephen G. Mayhew
Role of conformational dynamics and associated electrostaticand hydrogen bonding interactions in the regulation ofredox potentials in the Clostridium beijerinckii flavodoxin 183Richard P. Swenson, Mumtaz Kasim, Luke H. Bradley, Larry Druhan
Effects of pH on the 13C and ISN NMR spectra of the hydroquinoneof Desulfovibrio vulgaris flavodoxin and its G61A mutant 187Garry N. Yalloway, Stephen G. Mayhew, Sjef J. Boeren, Jacques Vervoort
Studies on urea-unfolding of flavodoxin and apoflavodoxin fromDesulfovibrio vulgaris (Hildenborough) 191Brian 6 Nuallain, Stephen G. Mayhew
3. Various Aspects
Flavin-linked redox components required for AhpC reductionin alkyl hydroperoxide reductase systems . 195Leslie B. Poole
Overexpression of the bifunctional chorismate sythase ofNeurospora crassa 203Karina Kitzing, Nikolaus Amrhein, Peter Macheroux
Amino acid substitutions near the FAD in NADH-cytochrome bs
reductase: roles of Arg*3 and Thr6* in the electron transfer 207Shigenobu Kimura, Masanori Kawamura, Takashi Iyanagi
Comparison of the spectral properties between pigMegasphaera elsdenii electron-transferring flavoproteins 211Kyosuke Sato, Yasuzo Nishina, Kiyoshi Shiga
Solvent isotope effects on electron transfer in xanthine oxidase 215Russ Hill, Robert F. Anderson
The family of A-type flavoproteins: new members and definitionof unique sequence fingerprints 219Claudio M. Gomes, Miguel Teixeira, Alain Wasserfallen
XX
Formation of ETF hydroquinone when complexed totrimethylamine dehydrogenase 223Mei-Huei Jang, Russ Hille, Nigel S. Scrutton
Evidence that Megasphaera elsdenii synthesises two differentelectron-transferring flavoproteins 227Zuhair Nasrallah, Hugh O'Neill, Stephen G. Mayhew
IV. 3D-Structures of Flavoproteins
Structural flavinology on the brink 233P. Andrew Karplus
Crystal structures of ,,unactivated" p-hydroxybenzoate hydroxylase 239Michel H. M. Eppink, Willem J. H. van Berkel, Alex Tepliakov,Herman A. Schreuder
NMR-studies on FMN-binding protein fromDesulfovibrio vulgaris (Miyazaki F) 243Masaya Kitamura, Hideo Inoue, Edwards Liepinsh, Gottfried Otting
Crystal structure of the respiratory fumarate reductase of reductaseof Shewanella putrefaciens MR-1:member of a novel flavocytochrome family 247David Leys, Terrance E. Meyer , Alexandre I. Tsapin,Michael A. Cusanovich, Jozef J. Van Beeumen
The domain structure of flavocytochrome c3 fromShewanella frigidiinarina 251S.L. Pealing, S.K. Chapman, P. Taylor, G.A. Reid, M.D. Walkinshaw
Structural biology of L-aspartate oxidase and polyamine oxidase 255Claudia Binda, Andrea Mattevi, G. Tedeschi, A. Negri,Rodolfo Federico, Riccardo Angelini
A new functional model for the Escherichia coli sulfite reductase:the aipi complex 259Jaques Coves, Mahel Zeghouf, Marc Fontecave
XXI
V. Flavins and Pyridine Nucleotides
Structural and functional properties of corn rootferredoxin-NADP+-reductase 265Alessandro Aliverti, Cristian Ferioli, Monica Spinola, Debora Raimondi,GiulianaZanetti, Casey Finnerty, RickFaber, P. Andrew Karplus
Role of the C-terminal tyrosine of plant ferredoxin-NADP+-reductasein NADP+ binding affinity and pyridine nucleotide specificity 269LucianoPiubelli, Alessandro Aliverti, GiulianaZanetti, Adrian K Arakaki,Nestor Carrillo, Eduardo A Ceccarelli, P. Andrew Karplus
Role of glutamic acid 139 in the catalytic mechanism offerredoxin-NADP+-reductase from Anabaena PCC7119 273Merche Faro, Milagros Medina, Carlos G6mez-Moreno,John K. Hurley, T.B. Brodi, Gordon Tollin
Characterisation of flavodoxin (ferredoxin) NADP+ oxidoreductase andflavodoxin; key components of electron transfer in Escherichia coli 277Lisa Mclver, Claire Leadbeater, Dominic J. Campopiano, Robert L. Baxter,Stephen K. Chapman and Andrew W. Munro
Sequence analysis and overexpression of putative NADH oxidasesfrom the hyperthermophilic archeaons Sulfolobus solfataricus andPyrococcus horikoshii 281Edward J. Crane III, Donald E. Ward, John van der Oost,Qunxin She, Roger Garrett
On new artificial mediator accepting NAD(P)H oxidoreductases fromClostridium thermoaceticum and Clostridiumformicoaceticum 285Helmut Giinther, Katrin Walter, Richard Feicht, Peter Kohler, Helmut Simon
Flavin reductase Fre from Escherichia coli: identification ofreaction intermediates and evidence for a new mode of bindingfor reduced pyrSdine nucleotides 289Vincent Niviere, Marc Fontecave, Maria A. Vanoni, Franck Fieschi
Determinants of cofactor specificity in Anabaena PCC7119ferredoxin-NADP+-reductase 293Jesus Tejero, Alejandra Luquita, Koert Grever, Carlos G6mez-Moreno,Milagros Medina, R. Perham
XXII
VI. Flavins and Light
1. Photochemistry, Blue Light Effects and Photolyases
Phototropin (nphl), a photoreceptor for phototropism, is anFMN-binding chromoprotein 299Winslow R. Briggs, John M. Christie, E. Knieb, Michael Salomon
DNA photolyase and cryptochrome 309Takeshi Todo
DCRY: A Drosophila photoreceptor protein implicated inlight entrainment of circadian rhythm 317Tomoko Ishiwaka, Takeshi Todo, Akira Matsumoto,Teiichi Tanimura, Shin Togashi, Ryu Ueda
Isolation and characterization of DNA photolyase/cytochromefamily in Zebra fish 321Yuri Kobayashi, Tomoko Ishikawa, Takeshi Todo,Hiromi Daiyasu, Hiroyuki Toh
2. Luciferase
Mechanism of reduced flavin transfer and complex formation betweenVibrio harveyi NADPH-FMN oxidoreductase and luciferase 325Shiao-Chun Tu, Benfang Lei, Mengyao Liu, Chih-Kwang Tang,Christopher Jeffers
Identification of P-flavin binding protein, and the genes forcobalamin-dependent methionine synthase andflavodoxin 1 in Vibrio flscheri 333Sabu Kasai
Modeling the intermediate IV of the luciferase reaction:characterization of the complex of 5-decylFMN-4a-OHwith Vibrio harveyi luciferase 337Benfang Lei, Qizhu Ding, Shiao-Chun Tu
XXIII
VII. Flavins and Oxygen
1. General Aspects
Coenzyme recognition by flavoprotein aromatic hydroxylases 343Willem J. H. van Berkel, Michel H. M. Eppink, Herman A. Schreuder
Wavin' flavins and passwords: dynamics and control in the reactionsof p-hydroxybehzoate hydroxylase 351Bruce A. Palfey, Kendra King Frederick, Rajit Basu, Dong XuDavid P. Ballou, Vincent Massey
2. Monooxygenases
Hydroxylation by flavin enzymes: evidence for NIH-shift mechanism 359Wolfgang Eisenreich, Claus Hultschig, Steffen Hartmann, Georg Fuchs,Adelbert Bacher, Sandro Ghisla
The intermediates involved in the catalytic reaction ofcyclohexanone monooxygenase 367Dawei Sheng, DavidP. BaHou, Vincent Massey
Catalytic properties of 2-hydroxybiphenyl 3-monooxygenase 371Winfried A. Suske, Hans-Peter Kohler, Willem J. H. van Berkel
Purification and some properties of acetophenone monooxygenase 375Marielle J.H. Moonen, Ivonne M.C.M. Rietjens, Willem J.H. van Berkel
Substrate and flavin activation in the hydroxylation catalyzed by/;-hydroxybenzoate hydroxylase: studies of the Lys297Met,Asn300Asp and Tyr385Phe forms reconstituted with 8rCl-FAD 379Mariliz Ortiz-Maldonado, Sara Aeschliman, David P. Ballou,Vincent Massey
Heterologous expression and kinetic characterization of humansqualene monooxygenase 383Brian P. Laden, Todd D. Porter
Novel two-component phenol hydroxylase from athermophilic Bacillus strain 387Ulrike Kirchner, R. Miiller, Willem J.H. van Berkel
XXIV
3. Various Aspects
Is charge-transfer complex formation essential for reductionof p-hydroxybenzoate hydroxylase? 391Barrie Entsch, Mariliz Ortiz-Maldonado, David P. Ballou
Single step analysis of catalysis of pyruvate oxidase fromLactobacillus plantarum. Kinetics, mechanism and regulation 395Kai Tittmann, Ralph Golbik, Gerhard Hiibner, Sandro Ghisla
Studies on the peroxide-reducing system of Thermits aquaticus. 401Catriona Logan, Stephen G. Mayhew
Converting a dehydrogenase into an oxidase 405Graeme A. Reid, Lars H. 0stergaard, Martin L. Goble, R. Moysey,Stephen K. Chapman
What protein features makep-hydroxybenzoate hydroxylasereact rapidly with oxygen? 409Willem J.H. van Berkel, Michel H.M. Eppink, Herman A. Schreuder,Mariliz Ortiz-Maldonado, Bruce A. Palfey, David P. Ballou, Barrie Entsch
VIII. Flavoproteins and MC=H-substrates"
1. A mine Dehydrogenation
Biochemical and structural characterization ofmonomeric sarcosine oxidase 415M.S. Jorns, M.A. Wagner, P. Trickey, F.S. Mathews
Substrate inhibition in trimethylamine dehydrogenase 423P. Roberts, J. Basran, E.K. Wilson, N.S. Scrutton, R. Hille
A novel heterotrimeric flavoprotein involved inbacterial nicotine catabolism 427Susann Schenk, Andre Hoelz, Karl Decker
High-level expression, structural, kinetic, and redox characterizationof recombinant human liver monoamine oxidase B 431Paige Newton-Vinson, Dale E. Edmondson
XXV
A mechanism for monoamine oxidase involving a redox-active disulfide 435Rona R. Ramsay
Involvement of mitochondria! matrix in the holoenzyme formationof dimethylglycine dehydrogenase 439Carmen Brizio, Ernesto Quagliariello, Maria Barile, Salvatore Passarella,Annegret Otto,, Roderich Brandsch
Hydrogen tunnelling in amine dehydrogenases frommethylotrophic bacteria 443Jaswir Basran, Peter Roberts, Nigel S. Scruttdn, Michael J. Sutcliffe
Investigating the mechanism of C-H bond breakage inheterotetrameric sarcosine oxidase from Arthrobacter sp. 1-IN 447RJ. Harris, N.S. Scrutton, M.J. Sutcliffe, R. Meskys
The reductive half-reaction of trimethylamine dehydrogenasewith trimethylamine 451Mei-Huei Jang, Russ Hille, Jaswir Basran, Nigel S. Scrutton
Interaction of FAD analogues with the C406A mutant apoenzymeof human liver monoamine oxidase A 455Ravi K. Nandigama, Dale E. Edmondson
2. a-Hydroxy Acid Dehydrogenases
X-ray studies of recombinant rat kidney long-chain hydroxy acid oxidaseand of the recombinant flavin-binding domain ofbakers yeast flavocytochrome b2 459L.M. Cunane, J.D. Barton, Zhi-wei Chen, F.S. Mathews, A. Belmouden,K.H.D. Le\ F. Lederer, F.E. Welsh, S.K. Chapman, G.A: Reid
On the mechanistic value of the dehydrohalogenation reaction ofp-halogeno a-hydroxy acids catalysed by FMN-dependent hydroxyacid-oxidizing enzymes: a mutational analysis with flavocytochrome b2 463Sabrina Bodevin, Florence Lederer
D-Lactate dehydrogenase model. Mechanism of the oxidation ofmandelic acid by functionalized flavin mimics with metal ions 467Hideaki Ohshiro, Shin-ichi Kondo, Yumihiko Yano
XXVI
Mechanistic roles of the conserved residue arginine 277in (S)-mandelate dehydrogenase from Pseudomonas putida 471Isabelle E. Lehoux, Bharati Mitra
The effects of mutation of Asp 180 of L-lactate monooxygenase fromMycobacterium smegmatis. Reduction of three mutants by L-lactateand production of hydrogen peroxide 475Stephen A Sanders, Ute Miih, Vincent Massey, Charles H. Williams Jr
Reaction mechanism of L-lactate oxidase from Aerococcus viridans 479Kazuko Yorita, Toshiyuki Watanabe, Hideo Misaki, Vincent Massey
The substrate specificity of L-mandelate dehydrogenase fromRhodotorula graminis 483Douglas J. Robertson, Stephen K. Chapman, Graeme A. Reid
(S)-mandelate dehydrogenase from Pseudomonas putida: The roleof the membrane-binding segment and Glycine 81 in the reactivitytoward oxygen 487Yang Xu, Bharati Mitra
3. Acyl-CoA Dehydrogenases
Evolution of an active site:The three-dimensional structures of Acyl-CoA dehydrogenases 491J.-J.P. Kim, M. Wang, R. Paschke, D. Roberts
Bioactivation of 5,6-dichloro-4-thia-5-hexenoyl-CoA by the medium chainAcyl-CoA dehydrogenase:Mechanism-based inactivation by a cytotoxic thioester 499J.F. Baker-Malcolm, C. Thorpe, M.W. Anders, M. Wang, J.-J.P. Kim
Synthesis, activity, and complexation effects of glutaryl-CoA analogswith glutaryl-CoA dehydrogenase 503Emily C. Ferguson, Lisa M. Sharpe, Shannon L. McKinney, Carrie L. Donley,Gregory K. Sewall, Amy L. Larsen, Colleen M. Byron
Redox potential and steady-state kinetic measurements of short-chainAcyl-CoA dehydrogenase (SCAD) active site mutants 507J.D. Pellett, A.K. Saenger, J.A. Fuchs, M.T. Stankovich,D.F. Becker
XXVII
Interactions of rat acyl-CoA oxidase with substrate analogsused as active-site probes 511Haruhiko Tamaoki, Chiaki Setoyama, Kyosuke Sato, Yasuzo Nishina,S. Tanase, Kiyoshi Shiga, Retsu Miura
Biochemical characteristics of recombinant human isovaleryl-CoAdehydrogenase pre-treated with ethylenediaminetetraacetate 515Al-Walid, A. Mohsen, Jerry Vockley
Probing the mechanism of medium-chain acyl-CoA dehydrogenase(MCAD) using spectrally active alternative-substrates and products 519Teresa R. Lamm, Marian Stankovich
Substrate chain length specificity of acyl-CoA dehydrogenases:studies on different mutants 523Burkhard Kiichler, Andy Nandy, Abdel Ghany and Sandro Ghisla
Probing the active site of the medium chain Ayl-CoA dehydrogenase:4-OH-cinnamoyl-CoA as a sensitive probe of polarization and ionization 527Irina Rudik, Colin Thorpe, Alasdair Bell, Peter Tonge
Substrate polarization of medium chain Acyl-CoA dehydrogenase(MCAD) • 531Avery W. Stephens, Kim M. Sabaj, Marian T. Stankovich,A. Bell, Peter J. Tonge
Medium chain Acyl-CoA dehydrogenase genetic defects:identification and partial characterisation of two new patient mutants 535A.G. Abdel Ghany, B. Kuchler, P. Bross, S. Ghisla
The crystal structur of human glutaryl-CoA dehydrogenase 539J.-J.P. Kim, M. Wang, R. Paschke
4. Amino Acid Oxidases
The reaction scheme of D-amino acid oxidase: substrate/productalignment for optimization of reductive and oxidative half-reactions 543Retsu Miura, Chiaki Setoyama, Yasuzo Nishima, Kiyoshi Shiga,Hisashi Mitzutani, Ikuko Miyahara, Ken Hirotsu
Reaction mechanism of flavin dehydrogenation by D-amino acid oxidase 551Loredano Pollegioni, Sandro Ghisla, Stephan Umhau, Gianluca Molla,Christopher M. Harris, Mirella S. Pilone
XXVIII
Structure and function of Rhodotorula gracitts D-amino acid oxidase1. Site-directed mutagenesis of tyrosines 223 and 238 559Gianluca Molla, Christopher M. Harris, Angelo Boselli, Silvia Sacchi,Mirella S. Pilone, Loredano Pollegioni
Structure and function of Rhodotorula gracilis D-amino acid oxidase2. Site-directed mutagenesis of arginine 285 and pH effects 563Viyiana Job, Christopher M. Harris, Davide Porrini, Gianluca Molla,Maria Cristina Vegezzi, Laura Motteran, Sandro Ghisla, Loredano Pollegioni,Mirella S. Pilone
Very high resolution crystal structure of D-amino acid oxidase.Insights into the reaction mechanism and mode of ligand binding 567S. Umhau, K. Diederichs, W. Welte, S. Ghisla, L. Pollegioni, G. Molla,D. Porrini, M.S. Pilone
Mutation in an hydrophobic sequence motif commonto N-hydroxylating enzymes 571Oliver Seth, Liliana Smau, Wolfram Welte, Sandro Ghisla, Peter Macheroux
Oligomerization and aggregation of lysine-N*-hydroxylase -an enzyme of the bacterial aerobactin biosynthesis 575Liliana Smau, Ohver Seth, Wolfram Welte, Sandro Ghisla,Peter Macheroux, Richard Thomas
Gender dependent tissue distribution of D-aspartate oxidasein Xenopus laevis 579Gabriella Tedeschi, Armando Negri, Emanuella Oungre, F. Cecilliani,Severino Ronchi, Giovanni Bernardini
Studies on the glycosylation of L-amino acid oxidase from the Malayanpit viper Calloselasma rhodostoma 583Peter Macheroux, Karina Kitzing, Michael Vetsch, Margarethe Sappelt,Sandro Ghisla, Margarete Schwarz, Manfred Kurfiirst
Role of the hydrogen-bonding network associated with isoalloxazinein the catalysis of D-amino acid oxidase 587Chiaki Setoyama, Retsu Miura, Yasuzo Nishina, Kiyoshi Shiga,Hisashi Mizutani, Ikuko Miyahara, Ken Hirotsu
Comparison of the amino acid sequence of Calloselasma rhodostomaL-amino acid oxidase to other FAD-dependent oxidases 591Oliver Seth, Lo-Chun Au, Sandro Ghisla, Claus Bollschweiler,Manfred Kurfiirst, Peter Macheroux
XXIX
Regulation of D-amino acid oxidase expression in the obligatoryaerobic yeast Rhodotorula gracilis 595Simona Rizzi, Gianluca Molla, Sonia Fantinato, Loredano Pollegioni
5. Dihydroorotate Dehydrogenases
Roles of three prosthetic groups in the tetrameric dihydroorotatedehydrogenase B from Lactococcus lactis 599Kaj Frank Jensen, Olof Bjornberg, Finn S. Nielsen, Mette Ottosen,Palle G. S0rensen, Paul Rowland, Sofie N0rager, Sine Larsen
Structure - function relationship of dihydroorotate dehydrogenases 603Sofie N0rager, Sine Larsen, Olof Bjornberg, Kaj Frank Jensen
The dihydroorotate dehydrogenases of Escherichia coli andLactococcus lactis represent two distinct families of the enzyme 607Olof Bjornberg, Kaj Frank Jensen, Anne Charlotte Griiner, Mette Ottosen,Palle Gravegaard S0rensen, Paul Rowland, Sofie N0rager, Sine Larsen
A sticky hydrogen atom in the reaction catalyzed by dihydroorotatedehydrogenase from Saccharomyces cerevisiae 611Douglas B. Jordan, John J. Bisaha, Michael A. Picollelli
Reduction reactions of two dihydroorotate dehydrogenases 615Bruce A. Palfey, Olof Bjornberg, Kaj Frank Jensen
Dihydroorotate dehydrogenase from the thermoacidophilic archaeonSulfolobus solfataricus is a cytosolic dimer 619Palle Gravegaard S0rensen, Gert Dandanell
Reversible unfolding and stability of dihydroorotate dehydrogenase Afrom Lactococcus lactis 623Mette Brimheim Ottosen, Olof Bjdrnberg, Kaj Frank Jensen,Lise Schack, Sine Larsen
6. Various Aspects
Cholesterol oxidase from Brevibacterium sterolicum and Streptomyceshygroscopicus: a covalent FAD binding vs. a non-covalent one 627Laura Motteran, Mirella S. Pilone, Loredano Pollegioni, Sandro Ghisla
XXX
Involvement of Aspl70 in catalysis of vanillyl-alcohol oxidase 631Robert H. H. van den Heuvel, Willem J. H. van Berkel,Marco W. Fraaije, Andrea Mattevi
Dynamics and spatial peculiarities of the mitochondria!NADH dehydrogenase. Spectroscopic studies. 635Nikolai Vekshin, Irina Sharova, Vladislav Sukharev
An iso-mechanism for nitroalkane oxidase: evidence for a slow protontransfer to solvent coupled to isomerization of the free reduced enzyme 639Giovanni Gadda, Paul F. Fitzpatrick
IX. Old Yellow Enzyme
New things about Old Yellow Enzyme 645Vincent Massey, Younus Mean, Dong Xu, Bette Jo Brown
Overexpression and characterization of 12-oxophytodienoic acidreductase from tomato; a member of the OYE family 655Jochen Strassner, Andreas Fiirholz, Peter Macheroux,Nikola Amrhein, A. Schaller, F. Schaller, E.W. Weiler
Study of the function of Old Yellow Enzyme in Saccharomyces cerevisiae 659Bette Jo Brown, Vincent Massey
The Old Yellow Enzyme family of flavoenzymes -comparison of substrate specificity and activity against explosives 663Richard E. Williams, Deborah Rathbone, Neil C. Bruce, Nigel S. Scrutton,Peter C.E. Moody, Stephen Nicklin
Structure and mechanism of an opiate-transforming redox enzyme:morphinone reductase 667Peter C.E. Moody, Daniel H. Craig, Nigel S. Scrutton, A.W. Munro,S.K. Chapman, Neil C. Bruce
Structure and mechanism of an explosive degrading enzyme:pentaerythritol tetranitrate reductase 671T. Barna, P.C.E. Moody, D.H. Craig, N.S. Scrutton, N.C. Bruce
XXXI
X. Flavoproteins and -SS-/-SH
An NADH oxidase functional as alkyl hydroperoxide reductase 677Youichi Niimura, Yoshitaka Nishiyama, Kouji Takeda, Hirokazu Tsuji,Kenji Ohnishi, Toshihiro Watanabe, Takeshi Nishino, Vincent Massey
Functional characterization of the N-terminus of AhpFby chimeric construction with TrR 681C. Michael Reynold, Leslie B. Poole
Egg white sulfhydryl oxidase: convergent evolution and catalysis ofdisulfide bond formation in proteins and peptides 685Karen L. Hoober, Colin Thorpe, D.L. Coppock
Functional and regulatory studies of two distinct NADH oxidasesfrom Streptococcus mutans 691M. Higuchi, Y. Yamamoto, L. Poole, M. Shimada, Y. Sato,N. Takahashi, Y. Kamio
Thioredoxin reductase from Plasmodiumfalciparum:interaction between the C-terminal cysteine residues and theactive site disulfide/dithiol 695Pan-Fen Wang, L. David Arscott, Charles H. Williams, Jr . 'Tim-Wolf Gilberger, Sylke Muller
Characterization of a glutathion amide reductase from the purplephototrophic bacterium Chromatium gracile, its altered substratespecificity, and involvement in detoxification of oxygen 699B. Vergauwen, Y. Guisez, R.G. Bartsch, T.E. Meyer, M.A. Cusanovich,J.J. van Beeumen
Tetryl as inhibitor and "subversive substrate" for human erythrocyteglutathione reductase 703V. Miskiniene, Z. Anusevicius, A. Maroziene, R. Kliukiene, H. Nivinskas,J. Sarlauskas, N. Cenas, K. Becker
XXXII
XI. Protein-Protein Interactions
Reaction and substrate recognition of the flavin reductase FRase Ifrom bioluminescent bacterium Vibrio fischeri:biochemistry and X-ray crystallography of FRase I 709W.C. Lee, T. Hirai, T.Kobori, H.Sasaki, H. Koike, M. Tanokura, S. Zenno,K. Saigo, T. Nishino, M.E.P. Murphy, E.T. Adman
The application of QM/MM techniques to flavoproteins:p-hydroxybenzoate hydroxylase (PHBH) 719Lars Ridder, Jacques Vervoort, Ivonne M. C. M. Rietjens
Structure and function of adrenodoxin reductase 729Gabriele A. Ziegler, Clemens Vonrhein, Georg E. Schulz, Israel Hanukoglu
Properties of NifL, a regulatory flavoprotein containing a PAS-domain 737R. Little, S. Hill, S. Perry, S. Austin, F. Reyes-Ramirez,R. Dixon, P. Macheroux
Molecular recognition between ferredoxin- NADP* reductase and itsprotein partners: role of charged and hydrophobic residues 741M. Martinez Jiilvez, I. Nogues, M. Medina, C. G6mez-Moreno,J.K. Hurly, G. Tollin
Analysis of a trimeric complex involving chorismate synthasefrom Bacillus subtilis 749Teresa Fitzpatrick, Nikolaus Amrhein, Peter Macheroux
Regulation of electron transfer in flavocytochrome b588 by theactivation domain of p61phox 753Yukio Nisimoto, Chang-Hoon Han, Shabnam Motalebi, David J. Lambeth
XII. Multidomain Flavoproteins
A new type of flavin adenine dinucleotide-binding resolved in themolybdo iron-sulfur-flavoprotein carbon monoxide dehydrogenasefrom Oligotropha carboxidovorans 759L. Gremer, Sabine Kellner, Ortwin Meyer,Holger Dobbek, Robert Huber
XXXIII
Studies on the iron-sulfur flavoenzyme adenosine 5'-phosphosulfatereductase from different organisms reveals a common structure 767and mechanismGunter Fritz, Thomas Buchert, Peter M. H. Kroneck
Properties of xanthine oxidase from human milk: the enzyme isgrossly deficient in molybdenum and substantially deficientin iron-sulphur centres 775Robert C. Bray, David Lowe, Ben Godber, Roger Harrison, Robert Eisenthal
Respiratory complex II from the thermoacidophilic archaeon,Sulfolobus sp. strain 7: genes and protein 779Toshio Iwasaki, Miho Aoshima, Asako Kounosu, Tairo Oshima
Crystal structur of xanthine oxidoreductase andERP assignment of Fe/S centers 783Cristofer Enroth, Bryan T. Eger, Emil F. Pai, Ken Okamoto, Toshio Iwasaki,Tomoko Nishino, Hiroyuki Hori, Takeshi Nishino
Azospirillum brasilense glutamate synthase: identification of substratesand cofactors binding sites by site-directed mutagenesis 787P. Morandi, B. Valzasina, C. Colombo, M.A. Vanoni, B. Curti
The mechanism of conversion from xanthine dehydrogenase to oxidaseof rat enzyme studied by site-directed mutagenesis 791Tomoko Nishino, Ken Okamoto, Hiroyuki Hori,Asako Kounosu, Takeshi Nishino
Studies of the bile acid inducible NADH: flavin oxidoreductase 795Martin Mewies, RussJClle
Azospirillum brasilense glutamate synthase: overproduction inE. coli and characterization of the recombinant enzyme 799M.A. Vanoni, S. Ravasio, H. Stabile, R. Bossi, G. Zanetti, B. Curti
Towards the natural electron donor of adenosine 5'-phosphosulfate (APS)reductase from Desulfovibrio desulfuricans Essex 803Thomas Buchert, Gunter Fritz, Peter M. H. Kroneck
xxxrv
XIII. Biosynthetic and Metabolic Aspects
19F NMR studies on lumazine synthase from Bacillus subtilis 809Markus Fischer, Karl Kugelbrey, Johannes Scheming, Mark Cushman
Reconstitution of 6-hydroxy-D-nicotine oxidase holoenzyme withN6-[N-(2-methylferrocene)-caproylamidoethyl]-FAD 813Roderich Brandsch, Carmen Brizio, Andreas F. Biickmann
Riboflavin transport and metabolism in isolated mitochondria 817Maria Barile, Carmen Brizio, Caterina De Virgilio, Salvatore Passarella
Synthesis and application of FAD analogs, functionalized atthe Imposition of the adenine 821A. Stocker, H.-J. Hecht, A.F. Buckmann, E. Katz, I. Willner,M. Dosch, C. Troupe
Biosynthesis of riboflavin: NMR studies on the 46-kDa dimeric protein,3,4-dihydroxy-2-butanone 4-phosphate synthase 825G. Richter, C. Krieger, M. Kelly, Y. Yu, L.J. Ball, P. Schmieder, H. Oschkinat
Investigation of the binding of 6,7-bis(trifluoromethyl)-8-ribityllumazinesto 15N-labeled lumazine synthase by REDOR-NMR 829Markus Fischer, Jon M. Goetz, Barbara Poliks, Daniel R. Studelska,Andreas GieBauf, Karl Kugelbrey, Mark Cushman, Jakob Schaefer
Biosynthesis of riboflavin: the reaction catalysed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without catalysis underphysiological conditions. 833Klaus Kis, KarlKugelbrey, Adelbert Bacher,
XIV. Medical Aspects
Medical aspects of flavins and flavoproteins - An outlook 839Kunio Yagi
Structural aspects of the flavoprotein domains of isoformsof nitric oxide synthase 845B.S. Masters, R.T. Miller, P. Martasek, L.J. Roman, J.S. Nishimura,S. Panda, D.E. Harris, P.M. Horowitz, T.M. Shea, J.C. Salerno,J. Zhang, J.J.P. Kim
XXXV
Family traits of FAD-containing disulfide reductases as drug targets 853K. Becker, S. Kanzok, R. Iozef, I. Tiirbachova, R.H. Schirmer
Disulfide reductases are destabilized by physiologic concentrationsofNADPH 857M. Schirmer, M. Scheiwein, S. Gromer, K. Becker, R.H: Schirmer
Construction of separate expression vectors for the catalytic core andthe N-terminal metal binding domain of Tn501 mercuric ion reductase 863Susan M. Miller
D-amino acid oxidase activity in the senescence-accelerated mouse 871Nobuko Ohishi, Shin-ichiro Yokoyama, Miyuki Kurata,Masashi Tanaka, Sadaaki Komura, Kunio Yagi
Riboflavin derivatives in food 875Anna Gliszczynska, Anna Koziolowa
A covalently bound flavin discovered in the reductase componentof a tetrahydrofuran-induced multicomponent monooxygenase 879Barbara Thiemer, Jan R. Andreesen, Thomas Schrader
Study on vanillyl-alcohol oxidase reveals a novel (covalent)flavoprotein family 883Marco W. Fraaije, Robert H.H. van den Heuvel,Willem J.H. van Berkel, Andrea Mattevi
Gene expression of D-amino acid oxidase in nervous system 887T. Kanamori, M. Obayashi, O. Jinnouchi, K. Kanda, Y. Urai,Y. Shishido, A. Suzue,.T. Sakai, K Fukui
Characterization of an adrenodoxin reductase-like protein ofMycobacterium tuberculosis 891A. Aliverti, F. Fischer, S. Pasquini, M.A. Vanoni, B. Curti, G. ZanettiR. Cantoni, M. Branzoni.G. Riccardi
Irreversible inhibitors of T. cruzi trypanothione reductase:Kinetic and crystallographic studies 895Susanne Bonse, R. Louise Krauth-Siegel, lime Schlichting, Gordon Lowe
Glutathione reductase of Plasmodiumfalciparum -Reductive and oxidative half reactions 899C.C. Bohme, R.H. Schirmer, K. Becker, L.D. Arscott, C.H. Williams Jr.
XXXVI
Cloning and mapping of the cDNA for human sarcosine dehydrogenase;a flavoenzyme defective in patients with sarcosinemia 903M. Eschenbrenner, M.S. Jorns
Author Index 909
Subject Index 917
Participants 931
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