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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