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Combining regio‐ and enantioselectivity of lipases for the preparation of ( R )‐4‐chloro‐2‐butanol
Author(s) -
Méndez Jonh J.,
Oromi Mireia,
Cervero Maria,
Balcells Mercè,
Torres Mercè,
Canela Ramon
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20339
Subject(s) - chemistry , rhizomucor miehei , candida rugosa , rhizopus oryzae , lipase , regioselectivity , hydrolysis , candida antarctica , aspergillus oryzae , butanol , organic chemistry , selectivity , alkyl , triacylglycerol lipase , chirality (physics) , enzyme , stereochemistry , catalysis , ethanol , fermentation , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.