Tetrahedron Letters p. 8379 - 8382 (1996)
Update date:2022-08-29
Topics:
Kroutil, Wolfgang
Mischitz, Martin
Plachota, Peter
Faber, Kurt
Biocatalytic hydrolysis of (±)-cis-2,3-epoxyheptane using lyophilized bacterial cells of Nocardia EH1 gave (2R,3R)-heptane-2,3-dil as the sole product in 79% yield and 91% e.e. at 100% conversion. The pathway of this deracemization was elucidated by 18OH2-labelling experiments using a partially purified epoxide hydrolase preparation and was shown to proceed in an enantioconvergent manner. Thus both substrate enantiomers were hydrolyzed via attack of [OH-] at the respective (S)-configurated C-atom with concomitant inversion of configuration.
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