Enantioselective Biocatalytic Reduction of Hexan-2-one, Catalyzed by Petroselinum crispum Cells

Abstract

A method for the synthesis of (2S)-(+)-hexan-2-ol, a precursor of a number of drugs, by the enantioselective biocatalytic reduction of a prochiral hexan-2-one, catalyzed by P. crispum cells, is proposed. Conditions for the synthesis of (2S)-(+)-hexan-2-ol within 48 h in a yield of 98% and an optical purity of 99% ee in the presence of isopropanol (3%) and in a yield of 85% and an optical purity of 90% ee in the presence of ethanol (2%) were found. It was shown that when the time of biotransformation in the presence of isopropanol and ethanol was prolonged to 144 h, the yield and optical purity of (2S)-(+)-hexan-2-ol significantly decrease, and the concentration of the starting ketone increases. With 1% isopropanol and 3 and 4% ethanol, only the starting hexan-2-one was present in the reaction mixture.