THEORETICAL-STUDY OF CONFORMATIONAL FEATURES OF NAD+ AND NADH ANALOGS - PROTONATED NICOTINAMIDE AND 1,4-DIHYDRONICOTINAMIDE

被引：62

作者：

WU, YD ^{[1
]}

HOUK, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 08期

关键词：

D O I：

10.1021/jo00060a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conformations of nicotinamide (N+) and 1,4-dihydronicotinamide (NH) have been studied by ab initio calculations at the MP2/6-31G*//6-31G* level. The amide group favors a cis conformation by about 1 kcal/mol for both N+ and NH. The rotational barrier for cis to trans interconversion is about 4 and 7 kcal/mol for N+ and NH, respectively. The amide group in the trans conformation is out of plane by about 20-degrees. The 1,4-dihydronicotinamide ring is slightly puckered and adopts a boat conformation. The calculated N-15 equilibrium isotope effect for hydride transfer is small, in agreement with experimental observations.

引用

页码：2043 / 2045

页数：3

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