Combining regio‐ and enantioselectivity of lipases for the preparation of ( R)‐4‐chloro‐2‐butanol

Abstract Preparation of 98% ee ( R )‐4‐chloro‐2‐butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435®), C. rugosa, Rhizomucor miehei (Lipozyme® IM)...

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Bibliographic Details
Published in:Chirality
Main Authors: Méndez, Jonh J., Oromi, Mireia, Cervero, Maria, Balcells, Mercè, Torres, Mercè, Canela, Ramon
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2006
Subjects:
Rugosa
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/chir.20339
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.20339
https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.20339
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Summary:Abstract Preparation of 98% ee ( R )‐4‐chloro‐2‐butanol was carried out by the enzymatic hydrolysis of chlorohydrin esters, using fungal resting cells and commercial enzymes. Hydrolyzes were carried out using lipases from Candida antarctica (Novozym 435®), C. rugosa, Rhizomucor miehei (Lipozyme® IM), Burkolia cepacia , and resting cells of Rhizopus oryzae and Aspergillus flavus . The influence of the enzyme, the solvent, the temperature, and the alkyl chain length on the selectivity of hydrolyzes of isomeric mixtures of chlorohydrin esters is described. Regioselectivity was higher than 95% for some of the tested lipases. Novozym 435 allowed preparation of the ( R )‐4‐chloro‐2‐butanol after 15 min of reaction at 30–40°C. Chirality, 2006. © 2006 Wiley‐Liss, Inc.

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