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 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 degrees C.
Méndez
Jonh J
JJ
Chemistry Department, Lleida University, Lleida, Spain.
Oromi
Mireia
M
Cervero
Maria
M
Balcells
Mercè
M
Torres
Mercè
M
Canela
Ramon
R
D001231:Aspergillus flavus / Q000378:metabolism; D000440:Butanols / Q000737:chemistry / Q000378:metabolism*; D008049:Lipase / Q000502:physiology*; D012233:Rhizopus / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013696:Temperature
D000440:Butanols; D008049:Lipase