Stereodirected Biocatalyzed Reduction of 4-Bromoacetophenone in (R)-(+)-1-(4-Bromophenyl)ethanol

Abstract

Enantiomerically pure secondary alcohols are valuable building blocks in the asymmetric synthesis of low-molecular bioregulators. For example, (S)- and (R)-1-(4-bromophenyl)ethanols are used in the synthesis of compounds for phototherapy and fluorescent diagnostics of malignant tumors. Previously, we demonstrated the possibility of stereoselective synthesis of (S)-(–)-1-(4-bromophenyl)ethanol from p-bromoacetophenone using biocatalysts based on Daucus carota and Petroselinum crispum plant cells. In this paper, we investigated the possibility of stereodirected synthesis of (R)-(+)-1-(4-bromophenyl)ethanol in the enantioselective bioreduction reaction of prochiral p-bromoacetophenone using Phaseolus vulgaris plant cells possessing R-reductase activity, and studied the possibility of intensification of bioreduction using exogenous reducing agents.