EXCHANGE OF AMIDE PROTONS - EFFECT OF INTRAMOLECULAR HYDROGEN-BONDING

被引：45

作者：

PERRIN, CL ^{[1
]}

DWYER, TJ ^{[1
]}

REBEK, J ^{[1
]}

DUFF, RJ ^{[1
]}

机构：

[1] UNIV PITTSBURGH, DEPT CHEM, PITTSBURGH, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 08期

关键词：

D O I：

10.1021/ja00164a037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetics of the exchange of the NH protons of a primary amide with intramolecularly hydrogen bonded protons has been studied by NMR saturation transfer methods. The base-catalyzed exchange is retarded ca. 30-fold by the hydrogen bonding. The exchange is considered to proceed by direct abstraction of the proton from the hydrogen bond. The acid-catalyzed exchange proceeds by the N-protonation mechanism, but there is no retardation due to hydrogen bonding. The significance of these results for NH proton exchange in peptides and proteins is discussed. © 1990, American Chemical Society. All rights reserved.

引用

页码：3122 / 3125

页数：4

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