Horse liver alcohol dehydrogenase-catalyzed enantioselective reduction of cyclic ketones: The effect of the hydrophobic side chain of the substrate on the stereoselectivity of the reaction

被引：5

作者：

Shigematsu, H ^{[1
]}

Matsumoto, T ^{[1
]}

Kawauchi, G ^{[1
]}

Hirose, Y ^{[1
]}

Naemura, K ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN SCI,DEPT CHEM,OSAKA 560,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期

关键词：

D O I：

10.1016/0957-4166(95)00396-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Horse liver alcohol dehydrogenase (HLADH)-catalyzed enantioselective reductions of alkyl3-oxocyclopentanecarboxylates, endo-5-acyloxybicyclo[2.2.1]heptan-2-ones and exo-5-acyloxybicyclo[2.2.1]heptan-2-ones gave the corresponding homochiral alcohols and ketones and the interaction between the hydrophobic side chain of the substrate and the hydrophobic zone in the active site played an important role in the specificity of the reduction. The stereoselectivities of the reactions were interpreted on the basis of the cubic space section model and a new rule, which contributes to development of a specificity analysis on the basis of the model, is introduced.

引用

页码：3001 / 3008

页数：8

共 12 条

[1] STEREOCHEMICAL ASPECTS OF SUBSTRATE SPECIFICITY OF HORSE LIVER ALCOHOL DEHYDROGENASE [J].