Epoxide hydrolase-mediated enantioconvergent bioconversions to prepare chiral epoxides and alcohols

Abstract

A number of epoxide hydrolase (EH)-mediated bioconversions have been developed to prepare single enantiomeric product from racemic substrates with a yield greater than 50%. Enantioconvergent hydrolysis using single or two EHs possessing complementary enantio- and regio-selectivity, EH-based chemoenzymatic reactions, and EH-triggered cascade-reactions have been developed for the preparation of chiral epoxides, epoxyalcohols, tetrahydrofuran derivatives and vicinal diols. All these bioconversions are based on stereochemical flexibilities of various EHs and can be used in total synthesis of biologically active compounds without the formation of unwanted enantiomers.

Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

“…Functioned as catalyzing the kinetic resolution and the enantioconvergent hydrolysis of racemic epoxides into the corresponding diols, the enzyme has been intensively explored in the past decades, and a number of excellent reviews focusing on its application in organic synthesis have been published [24,[131][132][133]. The cofactor-independent EH catalysis has several advantages, such as the broad substrate specificities with high regio-and enantioselectivity and activity in organic solvents, which leads to many successful applications [132].…”

“…Therefore, enantioconvergent processes are possible for EH-catalyzed reactions. In case of mono-substituted epoxides, it is common that the enantioconvergent reactions proceed via both the k 1 and k 4 pathways, leading to the (R)-diol in 100% theoretical yield [24,132,138].…”

Comparative homology modeling-inspired protein engineering for improvement of catalytic activity of Mugil cephalus epoxide hydrolase

“…Epoxide hydrolase (EH) catalyzes the enantioselective hydrolysis of racemic epoxides for preparing enantiopure epoxides and vicinal diols Lee 2008;Strauss et al 1999). Enantiopure epoxides and diols are useful starting materials for preparing more complex enantiopure pharmaceuticals (Archelas and Furstoss 2001).…”

One-pot biotransformation of racemic styrene oxide into (R)-1,2-phenylethandiol by two recombinant microbial epoxide hydrolases

“…Enantioconvergent biotransformations have been investigated to obtain yields greater than 50% [5,6]. In order to prepare single enantiomer from racemate, biotransformations for both enantiomers must proceed in enantio-and regiocomplementary fashions, and one enantiomer should be transformed with an inversion of chiral configuration (Fig.…”