Aqueous aldol catalysis by a nicotine metabolite

被引：162

作者：

Dickerson, TJ

Janda, KD

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 13期

关键词：

D O I：

10.1021/ja017774f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nornicotine, an endogenous tobacco alkaloid and minor nicotine metabolite, can catalyze aldol reactions at physiological pH. Catalysis appears to be due to a covalent enamine mechanism, an unprecedented reaction with small organic molecule catalysts in aqueous buffer. Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal catalysis. Substrate compatibility of this catalyst and its implications in vivo are discussed. Copyright © 2002 American Chemical Society.

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页码：3220 / 3221

页数：2

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