3-Hydroxyglutarate and β,γ-Epoxy Esters as Substrates for Pig Liver Esterase (PLE) and α-Chymotrypsin

Article abstract of DOI:10.1002/hlca.19870700118

The pH dependence of the α-chymotrypsin-catalyzed hydrolysis of dimethyl 3-hydroxyglutarate (3) has been studied.The e.e. was determined by HPLC analysis of diastereoisomeric camphanoic-acid derivatives.Kinetic resolution of the β,γ-epoxy esters 10 and 24 by pig liver esterase has been shown to provide an alternative access to chiral β-hydroxy esters and acids of high optical purity.By this latter method, the unnatural enantiomer of γ-amino-β-hydroxybutyric acid (GABOB) has been sinthesized.Finally, dimethyl meso-3,4-epoxyadipate (19) was hydrolyzed by pig liver esterase with almost 100 percent selectivity.