(S)-SELECTIVE RETROALDOL REACTION AND (R)-SELECTIVE BETA-ELIMINATION WITH AN ALDOLASE CATALYTIC ANTIBODY

被引:21
作者
REYMOND, JL
机构
[1] Department of Molecular Biology, Scripps Research Insitute, La Jolla, California, 92037
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 20期
关键词
ALDOLASES; ALDOL REACTIONS; CATALYSIS; CATALYTIC ANTIBODIES;
D O I
10.1002/anie.199522851
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The artificial aldolase assembled from ArCH2NH2 and antibody 72D4, which was raised against hapten 1, catalyzes the si‐selective aldol addition of acetone to aldehydes by an enamine mechanism. In the back reaction, the (4S)‐configurated aldols undergo a selective retroaldol reaction [Eq. (a)] and the (4R)‐configurated aldols eliminate water [Eq. (b)]. These results can be explained by conformational control of the imine intermediate. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:2285 / 2287
页数:3
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