Manipulating regioselectivity of an epoxide hydrolase for single enzymatic synthesis of (R)-1,2-diols from racemic epoxides

Chem Commun (Camb). 2020 Mar 3;56(18):2799-2802. doi: 10.1039/d0cc00283f.

Abstract

Both the activity and regioselectivity of Phaseolus vulgaris epoxide hydrolase were remarkably improved via reshaping two substrate tunnels based on rational design. The elegant one-step enantioconvergent hydrolysis of seven rac-epoxides was achieved by single mutants, allowing green and efficient access to valuable (R)-1,2 diols with high eep (90.1-98.3%) and yields.

MeSH terms

  • Alcohols / chemistry
  • Alcohols / metabolism*
  • Epoxide Hydrolases / chemistry
  • Epoxide Hydrolases / metabolism*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Phaseolus / enzymology*
  • Stereoisomerism

Substances

  • Alcohols
  • Epoxy Compounds
  • Epoxide Hydrolases