Methods in Enzymology

Volume 280

Vitamins and CoenzymesPart J

EDITED BY

Donald B. McCormickDEPARTMENT OF BIOCHEMISTR Y

EMORY UNIVERSITY

ATLANTA, GEORGIA

John W. SuttieDEPARTMENT OF BIOCHEMISTRY

UNIVERSITY OF WISCONSIN

MADISON, WISCONSIN

Conrad WagnerDEPARTMENT OF BIOCHEMISTRY

VANDERBILT UNIVERSITY AND VA MEDICAL CENTER

NASHVILLE, TENNESSEE

CONTRIBUTORS TO VOLUME 280 .

i x

PREFACE Xii i

VOLUMES IN SERIES x v

Section I. Pyridoxine, Pyridoxamine, Pyridoxal :Analogs and Derivative s

1 . Determination of Vitamin B 6 Vitamers and Metab- HARUHITO TSUGE

3

olites in a Biological Sampl e

2 . High-Performance Liquid Chromatography Deter- HERMANN J. MASCHER

1 2

mination of Total Pyridoxal in Human Plasm a

3 . Determination of 5-Pyridoxic Acid, 5-Pyridoxic J. DENNIS MAHUREN AN DAcid Lactone, and Other Vitamin B 6 Compounds STEPHEN P . COBURN

2 2

by Cation-Exchange High-Performance LiquidChromatograph y

4. Nuclear Magnetic Resonance in Study of Active DAVID E . METZLER

3 0

Sites of Pyridoxal-Dependent Enzyme s

5. Synthesis and Application of Pyridoxal Polyphos- TOSHIO Fuxul ANDphoryl Derivatives as Active-Site Probes for Nu- KATSUYUKI TANIZAWA

4 1

cleotide-Binding Enzyme s

6. Preparation of Vitamin B6-Peptide and Vitamin STANLEY STEIN ANDB 6-Peptide-Oligonucleotide Conjugates

TIANMIN ZHU

5 1

7. Preparation of Nonlabeled, Tritiated, and Deuter- JESSE F . GREGORY III ANDated Pyridoxine 5'-ß-D-Glucoside and Assay of HIDEKO NAKANO

5 8Pyridoxine-5'-ß-D-glucoside Hydrolas e

8. Enzymatic Preparation of Pyridoxine 4'- and 5'-a- YUKIO SUZUKI ,D-Glucosides

YUSUKE Doi ,KEI UCHIDA, ANDHARUHITO TSUGE

6 6

9. Formation of ß-Galactosides of Pyridoxine Using YUKIO SUZUKI AN DSporobolomyces singularis

KEI UCHIDA

71

Section II . Carbonyl Coenzymes: Pyruvyl Enzyme sand Quinoproteins

10 . Phosphatidylserine Decarboxylases : Pyruvoyl-De- WILLIAM DOWHAN

8 1

pendent Enzymes from Bacteria to Mammals

11. Production, Assay, and Occurrence of Pyrrolo- M . MISSET-SMITS ,quinoline Quinone

A. J . J. OLSTHOORN ,A . DEWANTI, ANDJ . A . DUINE

8 9

12. Amine-Oxidizing Quinoproteins

CHRISTA HARTMANN ANDWILLIAM S . MCINTIRE

98

13 . Gas Chromatographic-Mass Spectrometric Analy- OSAMU SUZUKI ANDsis of Pyrroloquinoline Quinone

TAKESHI KUMAZAWA

150

14. Monoclonal Antibodies Specific to Pyrroloquino- HIROSHI NARITA AN Dline Quinone

EMI MORISHITA

15 8

Section III . Nicotinic Acid: Analogs and Coenzymes

15. Determination, Purification, and Characterization ANDREE KLEMM ,

of a-NADH and a-NADPH

THOMAS STEINER ,UWE FLÖTGEN ,GERHARD A. CUMME, ANDANTON HORN

17 1

16. Affinity Labels for NAD(P)-Specific Sites

ROBERTA F . COLMAN

186

17 . Photoaffinity Labeling of NAD'-Linked Enzymes CHARLES MARK ENSOR AN DHSIN-HSIUNG TAI

204

18. Determining NAD Synthesis in Erythrocytes

VANNA MICHELI AN DSILVIA SESTINI

21 1

19 . Tissue NAD as a Biochemical Measure of Niacin ELAINE L . JACOBSON AN DStatus in Humans

MYRON K . JACOBSON

22 1

20 . Radioimmunoassay for Measuring Endogenous RICHARD M . GRAEFF ,Levels of Cyclic ADP-Ribose in Tissues

TIMOTHY F . WALSETH, ANDHON CHEUNG LEE

23 0

21. Purification of Human Nicotinamide-Mononucleo- GIuuo MAGNI ,tide Adenylyltransferase

MONICA EMANUELLI ,ADOLFO AMICI ,NADIA RAFFAELLI, AN DSILVERIO RUGGIERI

24 1

22 . Nicotinamide-Mononucleotide Adenylyltransfer- GIULIO MAGNI ,ases from Yeast and Other Microorganisms

NADIA RAFFAELLI ,MONICA EMANUELLI ,ADOLFO AMICI,PAOLO NATALINI, ANDSILVERIO RUGGIERI

248

23. Use of Biotinylated NAD to Label and Purify ADP- JIE ZHANG

25 5Ribosylated Proteins

24 . Preparation of Cyclic ADP-Ribose, 2'-Phospho-Cy- MYRON K . JACOBSON ,

clic ADP-Ribose, and Nicotinate Adenine Dinu- DONNA L . COYLE ,

cleotide Phosphate : Possible Second Messengers CHINH Q. Vu,of Calcium Signaling

HYUNTAE KIM, AND

ELAINE L. JACOBSON

26 5

25. Preparation of Low Molecular Weight Model Con- DANIEL CERVANTES-LAUREAN ,

jugates for ADP-Ribose Linkages to Protein

ELAINE L. JACOBSON, AND

MYRON K . JACOBSON

27 5

26 . Bioassay for Determining Endogenous Levels of TIMOTHY F . WALSETH ,

Cyclic ADP-Ribose

LONG WONG,

RICHARD M . GRAEFF, AN D

HON CHEUNG LEE

287

27 . Preparation of Cyclic ADP-Ribose Antagonists and TIMOTHY F . WALSETH ,

Caged Cyclic ADP-Ribose

ROBERT AARHUS ,

MARY E . GURNACK,

LONG WONG,

HANS-GEORG A. BREITINGER,

KYLE R. GEE, AND

HON CHEUNG LEE

294

28. Synthesis and Hydrolysis of Cyclic ADP-Ribose by HIROSHI OKAMOTO ,

Human Leukocyte Antigen CD38 : Inhibition of SHIN TAKASAWA ,

Hydrolysis by ATP and Physiological Significance AKIRA TOHGO ,

Kon NATA,

ICHIRO KATO, AND

NAOYA NOGUCHI

306

29. Large-Scale Production of Human CD38 in Yeast CYRUS B . MUNSHI,

by Fermentation

KATHRYN B . FRYXELL ,

HON CHEUNG LEE, AND

W . DALE BRANTON

31 8

30. Large-Scale Purification of Aplysia ADP-Ribosyl- HoN CHEUNG LEE,

cyclase and Measurement of Its Activity by Fluo- RICHARD M . GRAEFF,

rimetric Assay

CYRUS B . MUNSHI,

TIMOTHY F. WALSETH, AN D

ROBERT AARHUS

331

Section N. Flavins and Derivative s

31 . Urinary Riboflavin Determination by Cm Reversed- Sxix-I HUANG,

Phase Open-Column Chromatography

MARJORIE J. CALDWELL, AND

KENNETH L . SIMPSON

343

32_ Chemical Synthesis and Properties of 7a-Hydroxy- KuNIO MATSUI AN D

riboflavin

SABU KASAI

352

33 . Synthesis of N6-(2-Aminoethyl)-FAD, N 6 -(6-Car- ANDREAS F. BUCKMANN,boxyhexyl)-FAD, and Related Compounds

VICTOR WRAY, ANDACHIM STOCKER

36 0

34 . Biosynthesis of Riboflavin : 3,4-Dihydroxy-2-buta- G. RICHTER, C. KRIEGER ,none-4-phosphate Synthase

R. VOLK, K . KIs ,H. RITZ, E. GÖTZE, ANDA. BACHER

37 4

35 . Biosynthesis of Riboflavin : GTP Cyclohydrolase II, A. BACHER, G . RICHTER ,Deaminase, and Reductase

H. RITZ, S . EBERHARDT,M. FISCHER, AN DC . KRIEGER

38 2

36 . Biosynthesis of Riboflavin: Lumazine Synthase and A. BACHER,Riboflavin Synthase

S . EBERHARDT,M. FISCHER, S . MÖRTL,K . KIs, K. KUGELBREY,J. SCHEURING, ANDK. SCHOTT

38 9

37 . Measurements and Characteristics of Intestinal Ri- GIANGUIDO RINDI AN Dboflavin Transport

GIULIA GASTALDI

39 9

38 . Purification and Properties of FAD Synthetase DONALD B . MCCORMICK ,from Liver

MASANORI OKA ,DELORES M . BOWERS-KOMRO ,YUKIKO YAMADA, AN DHOLLY A . HARTMAN

407

39 . Determining Covalent Flavinylation

KARL DECKER ANDRODERICH BRANDSCH

413

40 . Purification and Characterization of 5'-Nucleoti- RITA S .-F . LEE ANDdase/FAD Pyrophosphatase from Human Pla- HENRY C . FORD

424cent a

41 . Syntheses and Applications of Flavin Analogs as YERRAMILLI V. S. N. MURTHYActive Site Probes for Flavoproteins

AND VINCENT MASSEY

436

AUTHOR INDEX 46 1

SUBJECT INDEX 483