DEOXYRIBOSE-5-PHOSPHATE ALDOLASE AS A CATALYST IN ASYMMETRIC ALDOL CONDENSATION

被引：100

作者：

CHEN, LR ^{[1
]}

DUMAS, DP ^{[1
]}

WONG, CH ^{[1
]}

机构：

[1] Scripps Res Inst, RES INST, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 02期

关键词：

D O I：

10.1021/ja00028a050

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.

引用

页码：741 / 748

页数：8

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