Premium
The effect of ethanol on the kinetics of lipase‐mediated enantioselective esterification of 4‐methyloctanoic acid and the hydrolysis of its ethyl ester
Author(s) -
Heinsman Nicole W. J. T.,
Valente Ana M.,
Smienk Henry G. F.,
van der Padt Albert,
Franssen Maurice C. R.,
de Groot Aede,
van ‘t Riet Klaas
Publication year - 2001
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/bit.10008
Subject(s) - hydrolysis , chemistry , enantiopure drug , ethanol , lipase , enantiomer , organic chemistry , enantioselective synthesis , kinetic resolution , alcohol , enzymatic hydrolysis , ethyl ester , catalysis , chromatography , enzyme
Abstract The Novozym 435® catalyzed esterification and hydrolysis reactions of 4‐methyloctanoic acid (ethyl ester) were investigated. In both the hydrolysis and esterification reactions, the increase of ethanol concentration led to an increase in enantiomeric ratio ( E ). For hydrolysis of the ethyl ester, the E ‐value increased from 5.5 [0% (v/v) EtOH] up to 12 [20% (v/v) EtOH]. In case of esterification, the E ‐value was already 16 [14% (v/v) EtOH] and rose to 57 [73% (v/v) EtOH]. When combining these results of esterification and hydrolysis, an enantiomeric ratio of 350 can be estimated for the sequential kinetic resolution of 4‐methyloctanoic acid. In this way, enantiopure 4‐methyloctanoic acid could be obtained after two consecutive reaction steps. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng 76: 193–199, 2001.