Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols

Dongliang Chang; Zunsheng Wang; Maarten F Heringa; Renato Wirthner; Bernard Witholt; Zhi Li

doi:10.1039/b300435j

Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols

Chem Commun (Camb). 2003 Apr 21:(8):960-1. doi: 10.1039/b300435j.

Authors

Dongliang Chang¹, Zunsheng Wang, Maarten F Heringa, Renato Wirthner, Bernard Witholt, Zhi Li

Affiliation

¹ Institute of Biotechnology, Swiss Federal Institute of Technology Zurich, ETH-Hoenggerberg, CH-8093 Zurich, Switzerland.

PMID: 12744319
DOI: 10.1039/b300435j

Abstract

Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase.

MeSH terms

Alcohols / chemical synthesis*
Cyclohexanes / chemistry
Cyclohexenes
Epoxide Hydrolases / chemistry*
Epoxy Compounds / chemistry*
Hydrocarbons, Alicyclic / chemistry*
Hydrolysis
Pyrrolidines / chemistry
Sphingomonas / enzymology*
Stereoisomerism

Substances

Alcohols
Cyclohexanes
Cyclohexenes
Epoxy Compounds
Hydrocarbons, Alicyclic
Pyrrolidines
cyclohexene oxide
Epoxide Hydrolases
pyrrolidine