A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents

For the purpose of carrying out smoothly enzymatic reaction of water-insoluble substrates in organic solvents, a new type of immobilized enzyme, a lipid-lipase aggregate, was developed. In order to prepare various kinds of lipid-lipase aggregates, 27 kinds of dialkyl ether-type phospholipid analogues were newly synthesized and used for the preparation of aggregates with lipase. Thus obtained lipid-lipase aggregates were found to catalyze the enantioselective hydrolysis of the (±)-α-acyloxy ester 2 much more efficiently than lipase immobilized with synthetic prepolymer (ENTP-4000) in water-saturated isopropyl ether. Namely. the reaction time became much shorter (2 to 3d for completion as compared with 21 d) and the chemical and optical yields of the reaction products were found to be high.