Methods in Enzymology Volume 142
Metabolism of Aromatic Amino Acids and Amines EDITED BY
Seymour Kaufman LABORATORY OF NEUROCHEMISTRY NATIONAL INSTITUTE OF MENTAL HEALTH BETHESDA, MARYLAND
FACHBEREICH BIOLOGIE (10, HochschuJe-Domwtadi -i Bibliothek 0 - 6100 D a r m s t a d t / B. *•
1987
ACADEMIC PRESS, INC. Harcourt Brace Jovanovich, Publishers
Orlando San Diego New York Austin Boston London Sydney Tokyo Toronto
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Table of Contents
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CONTRIBUTORS TO V O L U M E 142
xi
f
PREFACE
xvii
VOLUMES IN SERIES
xix
Section I. Catabolism of the Aromatic Amino Acids 1. Phenylalanine 4-Monooxygenase from Rat Liver
SEYMOUR KAUFMAN
2. Purification and Assay of Rat Liver Phenylalanine Ross SHIMAN 4-Monooxygenase
3 17
3. Phenylalanine 4-Monooxygenase from Human JEAN-PIERRE ABITA, Liver
FELICIENNE BLANDIN-SAVOJA, AND FRANCOISE REY
27
4. Phenylalanine 4-Monooxygenase from Bovine ANNE P. D0SKELAND, Liver
STEIN OVE D0SKELAND, AND TORGEIR FLATMARK
35
5. Phenylalanine 4-Monooxygenase from Chromo- HITOSHI FUJISAWA AND bacterium violaceum
HIROYASU NAKATA
44
6. Chromobacterium violaceum Phenylalanine 4- STEPHEN O. PEMBER, Monooxygenase
JOSEPH J. VILLAFRANCA, AND STEPHEN J. BENKOVIC
50
7. Tyrosine 3-Monooxygenase from Bovine Adrenal TOSHIHARU NAGATSU AND Medulla
8. Tyrosine 3-Monooxygenase from Rat Adrenals •
KAZUHIRO OKA
56
HITOSHI FUJISAWA AND SACHIKO OKUNO
63
9. Tyrosine 3-Monooxygenase from Rat Pheochro- A. WILLIAM TANK AND mocytoma
NORMAN WEINER— •
71
10. Tryptophan 5-Monooxygenase from Rat Brain HITOSHI FUJISAWA AND Stem
HIROYASU NAKATA
11. Tryptophan 5-Monooxygenase from Mouse Mas- HIROYUKI HASEGAWA AND tocytoma: High-Performance Liquid Chroma- ARATA ICHIYAMA tography Assay
83
88
12. Tryptophan 5-Monooxygenase from Mouse Mas- HITOSHI FUJISAWA AND tocytoma Clone P815
HIROYASU NAKATA
93
VI
TABLE OF CONTENTS
13. Dihydropteridine Reductase from Sheep Liver 14. Dihydropteridine Reductase from Bovine Liver
SEYMOUR KAUFMAN HIROYUKI HASEGAWA AND NOBUO NAKANISHI
15. NADPH-Specific Dihydropteridine from Bovine Liver
97
Reductase HIROYUKI HASEGAWA AND NOBUO NAKANISHI
103
111
16. Use of a Naphthoquinone Adsorbent for the Isola- FRANK A. FIRGAIRA, tiori of Human Dihydropteridine Reductase R. G. H. COTTON, I. JENNINGS, AND D. M. DANKS
17. Dihydropteridine Reductase from Sheep Brain
116
K. G. SCRIMGEOUR AND S. CHEEMA-DHADLI
127
18. 4-Hydroxyphenylpyruvate Dioxygenase from Pig DAVID J. BUCKTHAL, Liver
PATRICK A. ROCHE, THOMAS J. MOOREHEAD, BRIAN J. R. FORBES, AND GORDON A. HAMILTON
132
19. 4-Hydroxyphenylpyruvate Dioxygenase from Hu- SVEN LINDSTEDT AND man Liver
20. 4-Hydroxyphenylpyruvate
BIRGIT ODELHOG
Dioxygenase
from SVEN LINDSTEDT AND
Pseudomonas
21. 4-Hydroxyphenylpyruvate Avian Liver
BIRGIT ODELHOG
Dioxygenase
139
from J. H. FELLMAN
143
148
22. Mammalian Monophenol Monooxygenase (Tyro- VINCENT J. HEARING, JR. sinase): Purification, Properties, and Reactions Catalyzed
154
23. Monophenol Monooxygenase from Neurospora
KONRAD LERCH
165
THEODORE L. SOURKES
170
crassa 24. Aromatic-L-Amino Acid Decarboxylase
25. Aromatic-L-Amino Acid Decarboxylase from Pig CARLA BORRI VOLTATTORNI, Kidney
A N N A GIARTOSIO, AND CARLO TURANO
26. Indoleamine 2,3-Dioxygenase
179
RYOTARO YOSHIDA AND OSAMU HAYAISHI
188
27. Purification and Properties of Tryptophan Side KATSUJI TAKAI AND Chain Oxidase: Types I and II from Pseudo- OSAMU HAYAISHI monas
195
28. Kynurenine-Oxoglutarate Aminotransferase from MICHAEL C. TOBES Rat Kidney "
' 217 \
29. Arylformamidase from Streptomyces
parvulus
EDWARD KATZ, DALE B R O W N , AND M. J. M. HITCHCOCK
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TABLE OF CONTENTS 30. Tryptophan C-Methyltransferase of Streptomyces flocculus
MARILYN K. SPEEDIE
VU 235
31. Phenylalanine Ammonia-lyase from the Yeast CREED W. ABELL AND Rhodotorula glutinis
RONG-SEN SHEN
242
32. L-Phenylalanine Ammonia-lyase from Soybean EVELYN A. HAVIR Cell Suspension Cultures
248
33. Transamination of Aromatic Amino Acids in Es- CHARALAMPOS MAVRIDES cherichia coli
253
34. Aromatic-Amino-Acid Small Intestine
267
Aminotransferase
[35. Aromatic-Amino-Acid-Glyoxylate
•
from TOMOO NOGUCHI
Aminotrans- YOSHIKAZU TAKADA AND
ferase from Rat Liver
TOMOO NOGUCHI
36. Cathepsin T
273
HENRY C. P I T O T AND EIICHI GOHDA
279
Section II. Biosynthesis of the Aromatic Amino Acids 37. Synthesis of Tryptophan from Chorismate: Com- IRVING P. CRAWFORD parative Aspects
293
|38. Anthranilate Synthase from Fluorescent Pseudo- IRVING P. CRAWFORD monads
300
09. Dehydroquinate Synthase from Escherichia coli, SHUJAATH M E H D I , and Its Substrate 3-Deoxy-D-ara6mo-heptulo-
JOHN W. FROST, AND
sonic Acid 7-Phosphate
JEREMY R. KNOWLES
0. Shikimate Dehydrogenase from Escherichia coli
306
SUBHENDU CHAUDHURI, IAN A. A N T O N , AND J O H N R. COGGINS
1. 3-Dehydroquinate Dehydratase from Escherichia coli
.
SUBHENDU CHAUDHURI, K E N N E T H D U N C A N , AND JOHN R. COGGINS
2. The arom Multifunctional Enzyme from Neurospora crassa
315
320
JOHN R. COGGINS, MARTIN R. BOOCOCK, SUBHENDU CHAUDHURI, JOHN M. LAMBERT, JAMES L U M S D E N , GILLIAN A. N I M M O , AND D. DRUMMOND S. SMITH
§3. 3-Phosphoshikimate 1-Carboxyvinyltransferase from Escherichia coli
A N N LEWENDON AND JOHN R. COGGINS
325
342
Vlll
TABLE OF CONTENTS
44. 3-Phosphoshikimate
1-Carboxyvinyltransferase
from Pisum sativum 45. Shikimate Kinases from Escherichia coli K12
DAVID M. MOUSDALE AND
JOHN R. COGGINS
348
ROBERT DE FEYTER
355
46. Chorismate Synthase: A Bifunctional Enzyme in FRANK H. GAERTNER Neurospora crassa 47. Anthranilate Synthase-Anthranilate Phosphoribo- RONALD BAUERLE, syltransferase Complex and Subunits oiSalmo- JOHN HESS, AND nella typhimurium 48. Phosphoribosylanthranilate
362
SARAH FRENCH
366
Isomerase-Indole- KASPER KIRSCHNER,
glycerol-Phosphate Synthase from Escherichia HALINA SZADKOWSKI, coli
THEODORE S. JARDETZKY, AND VRENI HAGER
386
49. Tryptophan Synthase from Escherichia coli and EDITH WILSON MILES, Salmonella typhimurium
RONALD BAUERLE, AND SYED ASHRAFUDDIN AHMED
50. Tryptophanase from Escherichia coli B/U7-A
398
IRAJ BEHBAHANI-NEJAD, J. L. DYE, AND CLARENCE H. SUELTER
414
51. Purification of Chorismate, Prephenate, and JAMES A. CONNELLY AND Arogenate by HPLC
52. Chorismate Mutase-Prephenate from Esherichia coli
DANIEL L. SIEHL
422
Dehydratase BARRIE E. DAVIDSON
432
53. Chorismate Mutase-Prephenate Dehydrogenase BARRIE E. DAVIDSON AND from Escherichia coli GRAHAM S. HUDSON
440
54. Chorismate Mutase from Mung Bean and Sor- DAVID G. GILCHRIST AND ghum
JAMES A. CONNELLY
450
55. Chorismate Mutase from Streptomyces aureofa- HELMUT GORISCH ciens
463
56. The Postprephenate Biochemical Pathways to R. JENSEN AND R. FISCHER
472
Phenylalanine and Tyrosine: An Overview 57. Prephenate Aminotransferase
C. BONNER AND R. JENSEN
479
58. Arogenate Dehydrogenase
C-..BONNER AND R. JENSEN
48£
59. Arogenate Dehydratase
R. FISCHER AND R. JENSEN
49?
60. Prephenate Dehydrogenase (Monofunctional)
R. FISCHER AND R. JENSEN
50:
61. Prephenate Dehydratase (Monofunctional)
R. FISCHER AND R. JENSEN
50'
62. Arogenate Dehydrogenase from Phenylobacte- FRANZ LINGENS, Hum immobile
EBERHARD KELLER, AND BRIGITTE KELLER
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TABLE OF CONTENTS
IX
Section III. Methods of Determination and Metabolism of the Aromatic Amines 63. Catecholamine Measurements in Plasma by High- PAUL HJEMDAHL Performance Liquid Chromatography with Electrochemical Detection
521
64. Catecholamine Metabolite Measurements in ELISABETH MORIER-TEISSIER Mouse Brain Using High-Performance Liquid AND RICHARD RIPS 535 Chromatography and Electrochemical Detection: Comparison of a One-Column Technique with a Two-Column Switching Technique 65. Enzymatic Radioimmunoassay of Epinephrine, WILLIAM J. RAUM Norepinephrine, Metanephrine, and Normetanephrine 66. Quantitation of Catecholamine Metabolites by JERRY J. WARSH, Gas Chromatography-Mass Spectrometry with DAMODAR D. GODSE, AND Selected Ion Monitoring PETER P. Li
550
571
67. Arylalkylamine Af-Acetyltransferase from Mam- M. A. A. NAMBOODIRI, malian Pineal Gland R. DUBBELS, AND D. C. K L E I N
68. Hydroxyindole O-Methyltransferase
583
DAVID SUGDEN, VALENTIN C E N A , AND DAVID C. K L E I N
590
69. Dopamine /3-Monooxygenase from Bovine Adre- TORBJ0RN LJONES nal Medulla
596
70. Dopamine
603
/3-Monooxygenase
from
Human RONALD P. FRIGON
Plasma 71. Avian Dopamine /3-Monooxygenase 72. Assay and Purification
ROGER M. WEPPELMAN
608
of Liver Monoamine MOUSSA B. H. YOUDIM AND
Oxidase
MEIR TENNE
73. Preparation of the Flavin-Containing Aromatic JAMES I. SALACH AND • Amine Oxidases of Human Placenta and Beef WALTER WEYLER *: Liver s 74. Monoamine Oxidase A and B from Human CREED W. ABELL I Liver and Brain 75. Aromatic Amine Dehydrogenase from Alcaligenes faecalis
MITSUHIRO NOZAKI
76. Norepinephrine A/-Methyltransferase from Rabbit RAY W. FULLER Adrenal Glands |77. Amine N-Methyltransferases
617
627 638 650 655
SHERRY S. ANSHER AND WILLIAM B. JAKOBY
, .
660
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TABLE OF CONTENTS 78. Indoleamine A/-Methyltransferase from Rabbit RAFFAELE PORTA Lung
668
AUTHOR INDEX
675
SUBJECT INDEX
701
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