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Enzymatic Transformations; 61. Preparation of Enantiopure Trifluoromethyl‐Substituted Aromatic Epoxides and Vicinal Diols using the Aspergillus niger Epoxide Hydrolase‐Catalysed Resolution
Author(s) -
Deregnaucourt Justine,
Archelas Alain,
Barbirato Fabien,
Paris JeanMarc,
Furstoss Roland
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200606061
Subject(s) - enantiopure drug , chemistry , epoxide hydrolase , aspergillus niger , epoxide , kinetic resolution , stereochemistry , vicinal , substrate (aquarium) , circular dichroism , enzyme , organic chemistry , hydrolase , enantioselective synthesis , catalysis , biochemistry , oceanography , geology , microsome
The resolution of eight differently substituted trifluoromethylstyrene oxide derivatives was explored using the Aspergillus niger epoxide hydrolase. The obtained results indicate that all (but one) epoxides were efficiently processed by this enzyme, under very mild experimental conditions. The specific activity and the enantioselectivity of the enzyme against each substrate were determined. Circular dichroism analysis was also performed, allowing us to establish the absolute configuration of the products.