Combining regio- and enantioselectivity of lipases for the preparation of (R)-4-chloro-2-butanol
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...
Published in: | Chirality |
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Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2016
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Subjects: | |
Online Access: | http://hdl.handle.net/10459.1/58367 https://doi.org/10.1002/chir.20339 |
Summary: | 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. |
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