Methods in Enzymology

Volume XVIIB

Metabolism of Amino Acidsand Amines

Herbert Tabor

Celia White Tabor

CONTRIBUTORS TO VOLUME XVIIB xvii

PREFACE xXlii

l l

VOLUMES IN SERIES xxv

Section I . Histidine

147. Enzymes and Intermediates ofHistidin eBiosynthesis in Salmonella typhimurium

ROBERT G . MARTIN ,MARY ANNE BERBERICH ,BRUCE N . AMES,WARREN W . DAVIS ,

ROBERT F. GOLDBER(:ER, AN DJOSEPH D . YOURNO

3

148 . Histidine Degradation (Bacillus subtilis)

BORIS MAGASANIK ,EDVARDAS KAMINSKAS, AN D

YOSEF KIMHI

4 5

148a .Histidine Ammonia-Lyase

BORIS MAGASANIK ,

(Bacillus subtilis)

EDVARDAS KAMINSKAS, AN DJOSEF KIMHI

4 7

I48b.Urocanase (Bacillus subtilis)

BORIS MAGASANIK, EDVARDASKAMINSKAS, AND JOSEF KIMHI

5 1

148c . Imidazolonepropionic Acid Hydrolase(Bacillus subtilis)

BORIS MAGASANIK, EDVARDASKAMINSKAS, AND JOSEF KIMHI

55

148d .N-Formimino-L-glutamate Formimino -

hydrolase (Bacillus subtilis)

BORIS MAGASANIK, EDVARDAS

KAMINSKAS, AND JOSEF KIMHI

5 7

I49a .Histidine Ammonia-Lyas e

(Pseudomonas)

MATTHEW M . RECHLER AN DHERBERT TABOR

63

I49b.Histidine Ammonia-Lyas e(Pseudomonas)

CLAUDE B . KLEE

69

149c .Urocanase (Pseudomonas putida)

ALLEN T . PHILLIPS ANDDONNA J . GEORGE

73

149d .N-Formimino-L-glutamate Imino-hydrolase (Pseudomonas sp .)

R. B . WICKNER AN DH . TABOR

80

150. Urocanase (Beef Liver)

H . HASSALL AND D. M .

GREENBERG

84

151 . The Preparation and Properties o f

4(5)-Imidazolone-5(4)-propioni c

Acid

H . HASSALL AND D. M .

GREENBERG

89

152 . Imidazolonepropionic Acid Hydrolase

(Rat Liver)

SOLOMON H . SNYDER

92

153a .Preparation of Carbamylglutamic Acid

and Hydantoin-5-propionic Acid

H . HASSALL AND D . M .

GREENBERG

95

153b.Preparation and Properties of 4 -

Oxoglutaramic Acid

H . HASSALL AND D . M .

GREENBERG

97

154. The Separation of Histidine Degra -

dation Products and Related

Imidazoles by Paper Chromatog -

raphy and Paper Electrophoresis

H . HASSALL

9 9

155. Carnosine Synthetase (Chick Muscle)

GOVIND D . KALYANKAR AND

ALTON MEISTER

10 2

156 . Ergothioneine Degradatio n

(Escherichia coli)

JOHN B . WOLFF

10 5

Section II . Lysine and Diaminopimelic Aci d

157. Lysine Biosynthesis (Yeast)

HARRY P. BROQUIST

11 2

157a .Homocitrate Condensing Enzym e

(Homocondensing Enzyme, Homo -

citrate Synthase)

HARRY P. BROQUIST

11 3

157b.cis-Homoaconitase

HARRY P. BROQUIST

11 4

157c .Homoisocitric Dehydrogenase

HARRY P . BROQUIST

11 8

157d .a-Ketoadipate-Glutamate Amino -

transferase

HARRY P . BROQUIST

11 9

157e .Aminoadipate Reductase System

HARRY P . BROQUIST

120

157f .Aminoadipic Semialdehyde-Glutamate

Reductase

HARRY P . BROQUIST

12 1

157g.Saccharopine Dehydrogenase

HARRY P . BROQUIST

124

158. Pyruvate-Aspartic Semialdehyde Con -densing Enzyme (Escherichia coli)

JOSEPH G . SHEDLARSKI

129

159 . Dihydrodipicolinic Acid Reductase

(Escherichia coli)

HADASSAH TAMIR

13 4

160. Diaminopimelate Decarboxylase

(Escherichia coli)

PETER J . WHITE

14 0

161 . Diaminopimelate Decarboxylase

(Spirodela oligorhiza)

HENRY J . VOGEL AN DALICE P . HIRVONEN

14 6

162 . Diaminopimelic-Adding Enzym e

(Bacillus cereus)

YUSUKE MIZUNO AND EIJI ITO

15 0

163. Lysine Oxygenase (Pseudomonas)

TERUKO NAKAZAWA

15 4

164. S-Aminovaleramidase (Pseudomonasputida)

MARVIN S . REITZ ANDVICTOR W . RODWELL

15 8

165a .Glutaric Semialdehyde Dehydrogenase

(Pseudomonas putida)

YUNG-FENG CHANG AN D

ELIJAH ADAMS

16 6

165b.Preparation and Assay of GlutaricSemialdehyde

ELIJAH ADAMS AN D

YUNG-FENG CHANG

17 1

166. Pipecolic Acid

VICTOR W . RODWELL

17 4

167. &'-Piperideine-6-carboxylic Acid and a -

Aminoadipic Acid 5-Semialdehyde

VICTOR W . RODWELL

18 8

168a.Lysine Fermentation (Clostridium)

THRESSA C . STADTMAN ANDMARGARET A . GRANT

19 9

168b.L-ß-Lysine Mutase (Clostridium sticklandii)

THRESSA C . STADTMAN ANDMARGARET A . GRANT

20 6

168c .D-a-Lysine Mutase (Clostridium)

THRESSA C . STADTMAN AN DMARGARET A . GRANT

21 1

168d.Lysine-2,3-aminomutase

THOMAS P . CHIRPICH AND

H. A. BARKER

21 5

169 . L-Lysine-a-Ketoglutarate Amino -

transferase (Achromobacter liquidum)

KENJI SODA AND HARU O

MISONO

22 2

170 . Spectrophotometric Determinatio n

of Lysine

HENRY J . VOGEL AN DYOSHIRO SHIMURA

22 8

Section III . Nitrile s

171. ß-Cyanoalanine Synthase (Blue Lupine)

H . R . HENDRICKSON AND

E . E . CONN

233

172. Hydroxynitrile Lyase (Sorghum vulgare)

M . K . SEELY AND E . E . CONN

23 9

173. Ricinine Nitrilase

WILLIAM G . ROBINSON ANDROBERT H. HooK

24 4

Section IV . Proline and Hydroxyproline

174a.The Preparation of Animal Proline Oxidase(Rat Liver), and Its Use for the Prep -aration of A'-Pyrroline-5-carboxylate

HAROLD J . STRECKER

25 1

174b . Chemical Synthesis of A'-Pyrroline-5 -carboxylate

HAROLD J . STRECKER

25 4

174c . A i-Pyrroline-5-carboxylate Reductase(Calf Liver) (Reduction of A l-Pyrroline-5-carboxylate to Proline)

HAROLD J . STRECKER

25 8

174d .A'-Pyrroline-5-carboxylate Dehydro-genase (Ox Liver) (Oxidation of A' -Pyrroline-5-carboxylate to Glutamate)

HAROLD J . STRECKER

26 2

175 . Enzymes and Intermediates of Hydroxy -proline Degradation

ELIJAH ADAMS

266I . Animal Pathway 266

A. Preparation of A'-Pyrroline-3-hydroxy-5-carboxylic Acid 26 8B. Preparation of 4-Hydroxy-2-ketoglutaric Acid 27 3C. Preparation of 4-Hydroxyglutamic Acid 27 7D. DL-4-Hydroxy-2-ketoglutarate Aldolase (Rat Liver) 280

II . Bacterial Pathway 28 4A. Hydroxyproline-2-epimerase 28 6B. Allohydroxy-D-proline Oxidase 290C. Preparation of A i-Pyrroline-4-hydroxy-2-carboxylic Acid 29 4D. A'-Pyrroline-4-hydroxy-2-carboxylate Deaminase 296E. Preparation of a-Ketoglutaric Semialdehyde 299F. a-Ketoglutaric Semialdehyde Dehydrogenase 303

176 . Collagen Proline Hydroxylase (Rat Skin)

ROBERT E. RHOADS, NELSO NE . ROBERTS, AND SIDNEYUDENFRIEND

30 6

177 . D-Proline Reductase (Clostridium stick-landiz)

ROBERT H . ABELES

31 7

Section V . Serine

178. 3-Phosphoglycerate Dehydrogenas e(Escherichia colt)

LEWIS I . PIZER AND ETSUR OSUGIMOTO

32 5

179. Phosphoserine Aminotransferase (SheepBrain)

HELGA HIRSCH-KOLB ANDDAVID M . GREENBERG

331

180 . Serine Transhydroxymethylase (Rabbi tLiver)

LAVERNE SCHIRCH

33 5

181 . a-Methylserine Transhydroxymethylase(Pseudomonas)

EDITH WILSON MILES

34 1

182. L-Serine Dehydratase (Rat Liver)

M . SUDA AND H . NAKAGAWA

34 6

183 . L-Serine Dehydratase (Clostridium aci-diurica)

R . D . SAGERS AN DJ . E . CARTER

35 1

184. D-Serine Dehydrase (Escherichia cola)

WILLIAM G . ROBINSO NAND ROSALIND LABOW

356

185 . L-Serine 0-Sulfate Degrading System o fRat Liver

NORMAN TUDBALL AN DJOHN H . THOMAS

36 1

Section VI . Sulfur Amino Acid s

187. Methionine Biosynthesis (Hog Liver)

JOHN M . BUCHANAN

37 1

188. 1V 5 -Methyltetrahydrofolate-Homocystein e(Vitamin B 12) Methyltransferas e(Escherichia coli B)

ROBERT T . TAYLOR AN DHERBERT WEISSBACH

37 9

189. Methionine Biosynthesis (Yeast)

EARL BURTON ANDWARWICK SAKAMI

38 8

190. Enzymatic Synthesis of Radioactive S -Adenosyl-L-methionine

HERBERT TABOR ANDCELIA WHITE TABOR

39 3

191 . Assay of Tissue Levels of S-Adeno-sylmethionine

IRWIN J . KOPIN AN DRoss J . BALDESSARINI

39 7

192. S-Adenosylmethionine : L-HomocysteineS-Methyltransferase (Saccharomycescerevisiae)

STANLEY K . SHAPIRO

40 0

193. T3 and UV-T3-Induced S-Adenosyl-methionine Cleavage Enzyme (Esche -richia coli)

MALCOLM L . GEFTER

40 6

194. S-Adenosylhomocysteine Nucleosidas e(Escherichia cola)

JOHN A . DUERRE

41 1

195a. Trans-Sulfuration Reactions : Introduction

MARTIN FLAVIN

41 6

195b. Preparation of O-Succinyl-L-homoserine

MARTIN FLAVIN

41 8

I95c. Synthesis of O-Acetylhomoserine

SADAMU NAGAI AN DMARTIN FLAVIN

423

195d. Cystathionine y-Synthase (Salmonella)

MARSHALL KAPLAN AN DSTEPHEN GUGGENHEIM

42 5

195e. y-Cystathionase (Neurospora)

MARTIN FLAVIN AN DCLARENCE SLAUGHTER

433':.

195f. ß-Cystathionase (Salmonella)

STEPHEN GUGGENHEIM

43 9

195g. Homoserine Transacetylase (Neurospora)

SADAMU NAGAI ANDDOUGLAS KERR

,' -1142

195h. O-Acetylhomoserine Sulfhydrylase(Neurospora)

DOUGLAS KERR

44 6

195i. Miscellaneous Procedures Involved inTrans-Sulfuration

MARTIN FLAVIN

45 0

196 . Cystathionine Synthase (Rat Liver)

M . SuDA, H . NAKAGAWA ,AND H . KIMURA

454

197 . Cysteine Biosynthesis : Serine Transacetyl -ase and O-Acetylserine Sulfhydrylas e(Salmonella typhimurium)

NICHOLAS M . KREDICH ANDMICHAEL A . BECKER

45 9

198 . S-Alkyl-L-cysteine Lyase (Pseudomonas)

YASUTOMI NISHIZUKA

47 0

199. S-Alkyl-L-cysteine Sulfoxide Lyase[Allium cepa (Onion)]

SIGMUND SCHWIMMER

47 5

200 . Cysteamine Oxygenase (Horse Kidney)

D . CAVALLINI, R . SCANDURRAAND S. DUPRE

479

201 . Glutathione Biosynthesis

ELIZABETH Dorm MOO ZAND ALTON MEISTER

48 3

I. y-Glutamylcysteine Synthetase (Hog Liver) 48 4

II . Glutathione (Tripeptide) Synthetase (Yeast) 48 8201a. y-Glutamylcysteine Synthetase (Rat Kidney) MARIAN ORLOWSKI AN D

ALTON MEISTER

49 5

202 . Glutathione Reductase (Yeast)

ROBERTA F . COLMAN

500

203 . Glutathione Reductase (Escherichia colt')

C . H . WILLIAMS, JR.AND L . D . ARSCOTT

50 3

204 . Small-Scale Purification of 35S-Glutathione

ANTHONY V . FURANO

50 9

205 . Thiol-Disulfide Transhydrogenase (Yeast)

SADAMU NAGAI

51 0

206 . Glutathione-Insulin Transhydrogenas e(Steer Liver)

HENRY H . TOMIZAWA

51 5

207 . Sulfite Reductase (Bakers ' Yeast)

AKIO YOSHIMOTO, NoBUoNAIKI, AND RYO SATO

52 0

208. Methyl Viologen- and Ferredoxin-Linke dSulfite Reductases (Spinach)

KozI ASADA, GORO TAMURAAND ROBERT S . BANDURSKI

528

209. TPNH-Sulfite Reductase (Escherichia cola)

LEWIS M . SIEGEL AN DHENRY KAMIN

539

210. 3'-Phosphoadenosine-5'-phosphosulfat e(PAPS) Reductase (Yeast)

ROBERT S . BANDURSKI

54 6

Section VII. Threonine

211 . L-Threonine Deaminase-Biosyntheti c(Salmonella typhimurium)

R . O . BURNS

55 5

212 . L-Threonine Deaminase, Biosyntheti c(Bacillus subtilis)

G. W . HATFIELD ANDH. E . UMBARGER

56 1

213 . Threonine Deaminase-Biosyntheti c(Rhodopseudomonas spheroides)

PRASANTA DATTA

56 6

214 . Threonine Deaminase-Degradative (Clos-tridium tetanomorphum)

ATSUSHI NAKAZAWA

57 1

215 . Threonine Deaminase-Degradativ e(Escherichia cola)

YUTAKA SHIZUTA ANDMASANOBU TOKUSHIGE

57 5

216. L-Threonine Dehydrogenase (Arthrobacter)

D . MCGILVRAY AN DJ . G . MORRIS

58 0

217. Aminoacetone Synthase (Arthrobacter)

D . MCGILVRAY AN DJ . G . MORRIS

58 5

Section VIII . Amino Acid Oxidation and Racemizatio n

218a. Assay of Amino Acid Oxidase

DANIEL WELLNER AN DLOUISE A . LICHTENBERG

59 3

218b. L-Amino Acid Oxidase (Snake Venom)

DANIEL WELLNER

59 7

218c. L-Amino Acid Oxidase (Rat Kidney)

MINORU NAKANO AN DT. S. DANOWSKI

60 1

219 . Oxidative Decarboxylation of AminoAcids (Horseradish Peroxidase)

MENDEL MAZELIS

60 6

220 . n-Amino Acid Oxidase and Its Complexes(Hog Kidney)

KUNIO YAGI

608

221 . D-Amino Acid Dehydrogenase (Pseu-domonas fluorescens)

KINJI TSUKADA

62 3

222 . Amino Acid Racemase (Pseudomonasstriata)

KENJI SODA AN DTAKAHARU OSUMI

629

Section IX. Amino Acid Binding Protein s

222a . Leucine Binding Proteins fro mEscherichia coli

CLEMENT E . FURLONG AN DLEON A . HEPPEL

63 9

Section X. Amines

Amino Acid Decarboxylatio n

223 . Adenosylmethionine Decarboxylas e(Escherichia coli W)

R. B . WICKNER, C . W . TABOR,AND H . TABOR

64 7

224 . Aromatic L-Amino Acid Decarboxylase(Guinea Pig Kidney)

WALTER LOVENBERG

65 2

225 . Arginine Decarboxylase (Escherichiacoli B)

ELIZABETH A . BOEKER AN DESMOND E . SNELL

65 7

226. Histidine Decarboxylase (Lactobacillus 30a)

GEORGE W . CHANG AN DESMOND E . SNELL

66 3

227. Histidine Decarboxylase (Mammalian)

DOROTHEA AURES AN DROLF HÄKANSON

66 7

228. L-Lysine Decarboxylase (Bacteriumcadaveris)

KENJI SODA AND MITSUAK IMORIGUCHI

67 7

Amine Oxidation and Hydroxylation

229. Amine Oxidase (Pig Plasma)

E. BUFFONI AND H . BLASCHKO 68 2

230. Monoamine Oxidase (Rabbit Serum)

CHARLES M . MCEWEN, JR.

686

231 . Monoamine Oxidase (Human Seru mor Plasma)

CHARLES M . MCEWEN, JR.

69 2

232. Amine Oxidase (Beef Plasma)

KERRY T. YASUNOBU AN DRICHARD A . SMITH

698

233. Amine Oxidase (Aspergillus niger)

HIDEAKI YAMADA ANDOSAO ADACHI

705

234 . Mitochondrial Amine Oxidase (Mono-amine Oxidase) (Beef Liver)

KERRY T . YASUNOBU ANDBENEDICT GOMES

70 9

235 . Monoamine Oxidase(Pig Brain, Mitochondrial)

K. F. TIPTON

717

236 . Tyramine Oxidase (Sarcina lutea)

HIDEAKI YAMADA, HIDEHIKO

KUMAGAI AND TAKAYUK I

UWAJIMA

72 2

237. Putrescine Oxidase (Micrococcus rubens)

HIDEAKI YAMADA

72 6

238. Diamine Oxidase (Pea Seedling)

J . M . HILL

73 0

239 . Diamine Oxidase (Pig Kidney)

BRUNO MONDOVI, GIUSEPP EROTILIO, MARIA TERESACOSTA, AND ALESSANDR OFINAZZI AGRÖ

73 5

240. Sensitive Fluorometric and Radio -

metric Assays for Monoamine Oxidaseand Diamine Oxidase

SOLOMON H . SNYDER AND

EDITH D . HENDLEY

74 1

241 . Spermidine Dehydrogenase (Serratiamarcescens)

C . W . TABOR AN DP . D . KELLOGG

746

242 . Dopamine ß-Hydroxylase (Beef Adrenal)

SEYMOUR KAUFMAN

75 4

Methyltransferases

243 . Methyltransferase Enzymes in Biogeni cAmine Metabolism

JULIUS AXELROD

76 1

243a. Phenylethanolamine-N-Methyltrans-

ferase (Mammalian Adrenal Glands)

JULIUS AXELROD

76 1

243b. Hydroxyindole-O-Methyltransferase

(Bovine Pineal Gland)

JULIUS AXELROD

76 4

243c . Histamine-N-Methyltransferase (Pig Liver) JULIUS AXELROD

76 6

Imidazoleacetic Aci d

245 . 5-Phosphoribosyl- l -pyrophosphate :

Imidazole-4(5)-acetate Phosphoribosyl

Transferase (Rabbit Liver)

G . M . CROWLEY

770

246. Imidazoleacetate Monooxygenase

(Pseudomonas)

MITSUHIRO NozAKI

77 3

Acetylcholin e

247. Microdetermination of Acetylcholin-

esterase, Choline Acetyltransferase, an d

Choline

LINCOLN T . POTTER

778

248. Acetylcholinesterase (Electrophoruselectricus)

WALD LEUZINGER

78 2

249. Choline Acetyltransferase

A . K . PRINCE

78 8

250. Choline Acetyltransferase (Mammalia nBrain)

LINCOLN T . POTTER ANDVIVETTE A . S . GLOVER

79 8

Section XI. Amines (Continued)

Miscellaneou s

251. N-Acetyltransferase (Mammalian Liver)

WENDELL W . WEBER

805

252 . Diamine-a-Ketoglutarate Aminotrans -ferase (Escherichia cola)

KI-HAN KIM ANDT. T . TCHEN

81 2

253. Glutathionylspermidine Synthetase(Escherichia cola)

HERBERT TABOR ANDCELIA WHITE TABOR

81 5

254. Ethanolamine Deaminase (Clostridium sp .)

BARRY H . KAPLAN ANDE . R . STADTMAN

81 8

255. Serotonin Sulfokinase (Rabbit Liver)

KuNIO YAGI

825

256. Chemical Synthesis of N-Acetyl-1,4 -diaminobutane, N'-Acetylspermidine ,and IV8 -Acetylspermidine .

HERBERT TABOR, CELIAWHITE TABOR, AND LEOPOLDDE MEIS

829

257 . ß-(Pyrazolyl-IV)-L-Alaninase (Pseudomonas)

YASUTOMI NISHIZUKA

83 4

Amine Assays

258. Determination of Tissue Histamine byan Enzymatic Isotopic Assay

SOLOMON H . SNYDER

838

259. Fluorometric Assay of Histamine

P . A . SHORE

842

260. The Use of Dansyl Derivatives for theIdentification and Quantitation o fAmines

C . R. CREVELING ANDJ . W. DALY

846

260a . Automated Determination of Polyamines

DAVID R. MORRIS

850

Section XII . Clinical Applications

261a . Clinical Aspects of Arginase

MORTON K . SCHWARTZ

85 7

26 lb. Clinical Aspects of L-Asparaginase

MORTON K . SCHWARTZ

86 1

26Ic. Clinical Aspects of Aspartate and Alanin eAminotransferases

MORTON K . SCHWARTZ

86 6

261d. Clinical Aspects of Leucine Amino -peptidase

OSCAR BODANSKY

875

261e. Clinical Aspects of Ornithine Carbamyl

OSCAR BODANSKY

885Transferas e

26If. L-Histidine Ammonia-Lyase (Huma nStratum Corneum)

BERT N . LA Du, JR .

89 1

261g. Use of L-Histidine Ammonia-Lyase forthe Determination of L-Histidine

H . HASSALL

89 5

AUTHOR INDEX

89 9

SUBJECT INDEX

918

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