REDUCTION OF 2-SUBSTITUTED CYCLOHEXANONES BY SACCHAROMYCES-CEREVISIAE

Citation
M. Zarevucka et al., REDUCTION OF 2-SUBSTITUTED CYCLOHEXANONES BY SACCHAROMYCES-CEREVISIAE, Biocatalysis and biotransformation, 13(4), 1996, pp. 233-243
Citations number
25
Categorie Soggetti
Biology,"Biothechnology & Applied Migrobiology
ISSN journal
10242422
Volume
13
Issue
4
Year of publication
1996
Pages
233 - 243
Database
ISI
SICI code
1024-2422(1996)13:4<233:RO2CBS>2.0.ZU;2-H
Abstract
An enzymatic reduction of 2-substituted cyclohexanones mediated by Sac charomyces cerevisiae was studied with respect to the stereochemical c ourse and optical purity of the products. Reduction of ketones 1b-1f r esulted in separable diastereoisomeric mixtures of cis- and trans-ster eoisomers of 2-substituted cyclohexanols (2b-2f and 3b-3f) having the (S) absolute configuration at the chiral center bearing the hydroxyl f unctionality with high enantiomeric purity. Reduction of ketone 1a yie lded mixture of cis-(1S, 2R)- and trans-(1R,2R)-stereoisomers (2a and 3a) with lower enantiomeric purity. Changes in the nature of the C(2)- substituent affect the stereochemical course of the biotransformation. However, they significantly influenced the enantiomeric purity of the products. The diastereoselectivity of the process was studied as well ; high diastereoselectivity was observed with the substrates 1a, 1e an d 1f.