Microbiological Transformations. 33. Fungal Epoxide Hydrolases Applied to the Synthesis of Enantiopure Para-Substituted Styrene Oxides. A Mechanistic Approach

S. Pedragosa-Moreau; C. Morisseau; J. Zylber; A. Archelas; J. Baratti; R. Furstoss

doi:10.1021/jo960558i

Microbiological Transformations. 33. Fungal Epoxide Hydrolases Applied to the Synthesis of Enantiopure Para-Substituted Styrene Oxides. A Mechanistic Approach

J Org Chem. 1996 Oct 18;61(21):7402-7407. doi: 10.1021/jo960558i.

Authors

S. Pedragosa-Moreau¹, C. Morisseau, J. Zylber, A. Archelas, J. Baratti, R. Furstoss

Affiliation

¹ Groupe Biocatalyse et Chimie Fine, ERS 157 associée au CNRS, Faculté des Sciences de Luminy, Case 901, 163 avenue de Luminy, 13288 Marseille Cedex 9, France.

PMID: 11667667
DOI: 10.1021/jo960558i

Abstract

The biohydrolysis of differently para-substituted styrene oxide derivatives was studied, using whole cells of the fungi Aspergillus niger or Beauveria sulfurescens. These microorganisms proved to be equipped with epoxide hydrolases which are able to achieve these hydrolyses with high enantioselectivity. This allowed the preparation of the optically active epoxides and of the corresponding vicinal diols which were obtained with good to excellent enantiomeric purity. These two microorganisms proved to be enantiocomplementary. A mechanistic study, carried out using a crude lyophilized enzymatic extract from A.niger, indicated via Hammet coefficient plotting that this hydrolysis is very probably due to a general base-catalyzed process.