Jump to main content
Jump to site search

Issue 24, 1997
Previous Article Next Article

Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: kinetics of an enantioconvergent process

Abstract

Asymmetric biocatalytic hydrolysis of (±)-2,3-disubstituted oxiranes leading to the formation of vicinal diols in up to 97% ee at 100% conversion was accomplished by using the epoxide hydrolase activity of various bacterial strains. The mechanism of this deracemization was elucidated by 18OH2-labelling experiments using a partially purified epoxide hydrolase from Nocardia EH1. The reaction was shown to proceed in an enantioconvergent fashion by attack of OH at the (S)-configured oxirane carbon atom with concomitant inversion of configuration. A mathematical model developed for the description of the kinetics was verified by the determination of the four relative rate constants governing the regio- and enantio-selectivity of the process.

Back to tab navigation

Article type: Paper
DOI: 10.1039/A704812B
Citation: J. Chem. Soc., Perkin Trans. 1, 1997, 3629-3636
  •   Request permissions

    Deracemization of (±)-2,3-disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: kinetics of an enantioconvergent process

    W. Kroutil, M. Mischitz and K. Faber, J. Chem. Soc., Perkin Trans. 1, 1997, 3629
    DOI: 10.1039/A704812B

Search articles by author

Spotlight

Advertisements