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Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids
Author(s) -
Hongwei Yu,
Jinchuan Wu,
Chi Bun Ching
Publication year - 2004
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.20078
Subject(s) - candida rugosa , chemistry , ionic liquid , lipase , kinetic resolution , catalysis , ibuprofen , chirality (physics) , solvent , organic chemistry , medicinal chemistry , enzyme , enantioselective synthesis , medicine , pharmacology , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Candida rugosa lipase‐catalyzed esterification of ibuprofen with 1‐propanol was conducted in seven ionic liquids and the results were compared with those in isooctane. Although the enzyme showed comparable or higher activity in some ionic liquids compared to that in isooctane, only in the case of [BMIM]PF 6 was the enantioselectivity ( E = 24.1) almost twice that ( E = 13.0) of isooctane. In another six ionic liquids the enzyme enantioselectivity was much poorer ( E = 1.1–6.4). At the same conversion of 30%, E of [BMIM]PF 6 is more than triple that of isooctane. The lipase stability in [BMIM]PF 6 was improved by 25% of that in isooctane. It was concluded that [BMIM]PF 6 could be applied to substitute the conventional organic solvent (isooctane) in the esterification of ibuprofen. Chirality 17:16–21, 2005. © 2004 Wiley‐Liss, Inc.