Chiral induction in cyclopentyl-derived 1,3-meso-diesters: enantioselective hydrolyses with electric eel acetylcholinesterase

被引：9

作者：

Deardorff, DR ^{[1
]}

Amador, RB ^{[1
]}

Morton, JW ^{[1
]}

Kim, HY ^{[1
]}

Taniguchi, CM ^{[1
]}

Balbuena, AA ^{[1
]}

Warren, SA ^{[1
]}

Fanous, V ^{[1
]}

Choe, SWT ^{[1
]}

机构：

[1] Occidental Coll, Dept Chem, Los Angeles, CA 90041 USA

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 11期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0957-4166(99)00236-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Eight 1,3-meso-diesters derived from a common cyclopentyl backbone were exposed to the hydrolase enzyme acetylcholinesterase from Electrophorus electricus. All eight compounds were hydrolyzed by the enzyme. The overall enantioselectivities were quite high, and the resulting e.e.s were generally >90%. The absolute configurations of the product monoesters were determined through stereochemical correlation. These data revealed that the preferred site for enzymatic hydrolysis in seven of the substrates was the pro-S ester function, with pro-R cleavage detected in the eighth. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2139 / 2152

页数：14

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