Zdeněk Wimmer

Reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae under aerobic and anaerobic conditions

Abstract The influence of aerobic and anaerobic conditions on the enzymatic reduction of 2-substituted cyclohexanones by Saccharomyces cerevisiae was studied. The investigation resulted in the synthesis of cis-(1S,2S)- and trans-(1S,2R)-enantiomers as the major components in the respective cis- and transisomers of 2-substituted cyclohexanols obtained. Changes between aerobic and anaerobic conditions did not affect the stereochemical course of the biotransformation with respect to the stereochemistry of the major components of the alcohols.

ByDioscorea deltoidea free and immobilized plant cells

Summary2-(4-methoxybenzyl)-1-cyclohexanone (1) was converted to its glucoside (4,5) via corresponding alcohols (3,4) usingDioscorea deltoidea Wall. free and immobilized plant cells.

Biotransformation of 2-(4-methoxybenzyl)-l-cyclohexanone by cell cultures ofSolatium aviculare

During the search for compounds with insect juvenile hormone activity, the biotransformation of 2-(4-methoxybenzyl)-l-cyclohexanone, of 2-(4-methoxybenzyl)-l-cyclohexanone ethylene acetal and of both isomers of 2-(4-methoxybenzyl)-l-cyclohexanol by plant cells was examined. The compounds were metabolized by cell suspension culture of Solatium aviculare Forst. The reaction conditions were optimized and the metabolic products isolated and identified. A scheme of biotransformation pathway has been proposed.

Stereochemistry of the enzymatic reduction of 2-(4-Methoxybenzyl)-1-cyclohaxanone by means of Solanum aviculare cells in vitro

During the investigation of chemical properties of the dicyclic system of insect juvenile hormone analogues, biotransformation of 2-(4-methoxybenzyl)-1-cyclohexanone (1) by plant cell cultures was studied. Among other components, the cis-(1S, 2S)- and cis-(1R, 2R)-2-(4-methoxybenzyl)-1-cyclohexanol enantiomers 2a and 2b were found in the reaction mixture. Higher stereoselectivity of the biotransformation was observed for trans-(1S, 2R)-enantiomer 3a formation, which occurred in at least 60% of calculated enantiomeric excess.