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

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2007
Author
Méndez, Jonh Jairo
Oromí Farrús, Mireia
Cervero, Maria
Balcells Fluvià, Mercè
Torres i Grifo, Mercè
Canela i Garayoa, Ramon
Suggested citation
Méndez, Jonh Jairo; Oromí Farrús, Mireia; Cervero, Maria; Balcells Fluvià, Mercè; Torres i Grifo, Mercè; Canela i Garayoa, Ramon; . (2007) . Combining regio- and enantioselectivity of lipases for the preparation of (R)-4-chloro-2-butanol. Chirality, 2007, vol. 19, núm. 1, p. 44–50. https://doi.org/10.1002/chir.20339.
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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.
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http://hdl.handle.net/10459.1/58367
DOI
https://doi.org/10.1002/chir.20339
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Chirality, 2007, vol. 19, núm. 1, p. 44–50
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