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Enantioselective esterification reaction using immobilized Candida rugosa lipase on poly( N ‐vinyl‐2‐pyrrolidone‐ co ‐styrene) hydrogel
Author(s) -
Harun A.,
Basri M.,
Ahmad M. B.,
Salleh A. B.
Publication year - 2004
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.20342
Subject(s) - candida rugosa , chemistry , lipase , enantioselective synthesis , vinyl acetate , styrene , polymer chemistry , solvent , chloroform , monomer , organic chemistry , catalysis , copolymer , polymer , enzyme
Lipase from Candida rugosa was immobilized on poly( N ‐vinyl‐2‐pyrrolidone‐ co ‐styrene) hydrogel (poly‐(VP‐ co ‐ST)) with ethylene dimethacrylate and α,α'‐azoisobutyronitrile, which act as crosslinker and initiator, respectively. Three different compositions of monomers were used, namely VP(%):ST(%), 10:90, 50:50, and 70:30 (wt(%)/wt(%)). The immobilized lipases were used in the enantioselective esterification of ( R , S )‐2‐(4‐chlorophenoxy)‐propanoic acid with n ‐tetradecanol. The optimum reaction condition of the enantioselective esterification for the native lipase and the poly(VP‐ co ‐ST) hydrogel immobilized lipases was determined with respect to temperature, solvents, and initial water activity ( a w ). The optimum temperature obtained was 40°C, with the poly(VP‐ co ‐ST) hydrogel immobilized lipase VP(%)/ST(%):10:90 showing the highest enantiomeric excess. In the solvent effect studies, the best solvents for high enantioselectivity were chloroform and carbon tetrachloride. In the a w studies, optimum α w for NL, VP(%):ST(%), 10:90, and 50:50 was 0.328, while for VP(%):ST(%), 70:30, it was 0.55. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 3381–3386, 2004