Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase

Abstract

The synthesis of enantiopure epoxides, as well as their corresponding vicinal diols is an actively pursued area of research. This is due to the fact that these compounds are essential chiral intermediates for the synthesis of bioactive products in the pharmaceutical and agrochemical industries. Therefore, the developments of efficient and cost effective processes for the preparation of these chiral molecules in enantiopure form are of importance. Epoxide hydrolase has emerged as an important enzyme for the asymmetric synthesis of enantiopure epoxides and diols via biocatalytic hydrolytic kinetic resolution (HKR) and enantioconvergent hydrolysis of racemic epoxides. The hydrolytic kinetic resolution of racemic epoxides provides a single enantiomer of the remaining epoxide and a single enantiomer of the formed diol whereas biocatalysts with complementary enantioselectivities and opposite regioselectivities provide the enantiopure diol as the only product, through enantioconvergent hydrolysis.