IMPROVEMENT OF ENANTIOSELECTIVE ENZYMATIC ESTER HYDROLYSIS IN ORGANIC-SOLVENTS

A method is presented to improve the enzymatic enantioselective hydrolysis of chiral esters in water-saturated organic solvents. It is shown that addition of a non-reactive amine to the reaction mixture leads to the formation of an ion-pair with the produced carboxylic acid. Yield and enantiomeric excess are increased in lipase catalyzed kinetic resolutions of methyl 2-chloropropionate and glycidyl butyrate in various solvents. Chemical background hydrolysis was reduced with respect to aqueous solvents. A second phase was formed during reaction in apolar solvents, due to ion-pair formation, which may facilitate the isolation of the desired compound.