Transient species in the stepwise interconversion of NADH and NAD+

被引：134

作者：

Gebicki, J ^{[1
]}

Marcinek, A ^{[1
]}

Zielonka, J ^{[1
]}

机构：

[1] Tech Univ Lodz, Inst Appl Radiat Chem, PL-90924 Lodz, Poland

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2004年 / 37卷 / 06期

关键词：

D O I：

10.1021/ar030171j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two mechanisms of the interconversion of NADH and NAD(+) in the coenzyme itself and in its analogues are discussed: a one-step hydride transfer and a stepwise electron-proton-electron transfer. Direct characterization of the transient species in the stepwise process and inversion of the stability order of the keto and enol tautomers is presented. The nonenzymatic and enzyme-mediated reactions of selected pyridinium salts that affect the NADH reversible arrow NAD(+) equilibrium are discussed in terms of their potential cytotoxicity.

引用

页码：379 / 386

页数：8

共 55 条

[1] THE REDUCTION OF THIOKETONES BY A MODEL FOR A COENZYME
ABELES, RH
HUTTON, RF
WESTHEIMER, FH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (03) : 712 - 716
[2] 3,6-diamino-10-methylacridan: Uncharged precursor of acriflavine and its unique antimicrobial activity
Adamus, J
Gebicki, J
Ciebiada, I
Korczak, E
Denys, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (16) : 2932 - 2933
[3] PHOTOCHEMICAL AND RADIOLYTIC CLEAVAGE OF 10-METHYLACRIDINE DIMER IN SOLUTIONS AND CRYOGENIC GLASSES
ADAMUS, J
ROGOWSKI, J
MICHALAK, J
PANETH, P
GEBICKI, J
MARCINEK, A
PLATZ, MS
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1993, 6 (04) : 254 - 256
[4] MECHANISM OF ONE-ELECTRON OXIDATION OF NAD(P)H AND FUNCTION OF NADPH BOUND TO CATALASE
ALMARSSON, O
SINHA, A
GOPINATH, E
BRUICE, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) : 7093 - 7102
[5] OXIDATION OF 10-METHYLACRIDAN, A SYNTHETIC ANALOG OF NADH, AND DEPROTONATION OF ITS CATION RADICAL - CONVERGENT APPLICATION OF LASER FLASH-PHOTOLYSIS AND DIRECT AND REDOX CATALYZED ELECTROCHEMISTRY TO THE KINETICS OF DEPROTONATION OF THE CATION RADICAL
ANNE, A
HAPIOT, P
MOIROUX, J
NETA, P
SAVEANT, JM
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (06) : 2370 - 2377
[6] DYNAMICS OF PROTON-TRANSFER FROM CATION RADICALS - KINETIC AND THERMODYNAMIC ACIDITIES OF CATION RADICALS OF NADH ANALOGS
ANNE, A
HAPIOT, P
MOIROUX, J
NETA, P
SAVEANT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) : 4694 - 4701
[7] RADICAL-CATION ACIDITIES IN SOLUTION AND IN THE GAS-PHASE
BORDWELL, FG
CHENG, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) : 1792 - 1795
[8] Low nicotinamide mononucleotide adenylyltransferase activity in a tiazofurin-resistant cell line: effects on NAD metabolism and DNA repair
Boulton, S
Kyle, S
Durkacz, BW
[J]. BRITISH JOURNAL OF CANCER, 1997, 76 (07) : 845 - 851
[9] REACTIVITY OF BIOLOGICALLY IMPORTANT REDUCED PYRIDINES .6. LACK OF THROUGH-RESONANCE STABILIZATION IN THE FERRICYANIDE-MEDIATED OXIDATION OF SUBSTITUTED 1-PHENYL-1,4-DIHYDRONICOTINAMIDES
BREWSTER, ME
KAMINSKI, JJ
GABANYI, Z
CZAKO, K
SIMAY, A
BODOR, N
[J]. TETRAHEDRON, 1990, 46 (02) : 319 - 324
[10] BRUHLMANN U, 1974, J AM CHEM SOC, V96, P6169

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