Enantioselective Acetylation of an α-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents

Abstract

Phospholipids of a new type having ω-cyclohexyltridecyl groups were synthesized in order to investigate the influence of the structure of lipophilic part of phospholipids upon the enzymatic reaction. Enantioselective acetylation of an α-hydroxy ester was carried out in the presence of lipid-lipase aggregates bearing O-ω-cyclohexyltridecyl and O-hexadecyl groups. The chemical yield of α-acetoxy ester was improved by using lipid-lipase aggregates compared to the case of enzymatic reaction using native lipase OF-360 from Candida cylindracea. It was found that the influence of the ω-cyclohexyltridecyl group on the chemical and optical yields of α-acetoxy ester was essentially the same as that to the hexadecyl group.