Kinetic resolution of rac-2-pentanol catalyzed by Candida antarctica lipase B in the ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide.
The ionic liquid, l-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide ([Bmim] [NTf2]), was used as a reaction medium for the kinetic resolution of rac-2-pentanol catalyzed by free Candida antarctica lipase B, using vinyl propionate at 2% (v/v) water content. The synthetic activity of lipase in [Bmim] [NTf2] was up 2.5-times greater than in hexane, and showed high enantioselectivity (ee > 99.99%). The optimal temperature and pH were 60 degrees C and 7, respectively. A decrease in water activity (aw) produced a decay in synthetic activity, and an exponential increase in selectivity.
Noël
Marilyne
M
Departamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, P.O. Box 4021, E-30100 Murcia, España.
Lozano
Pedro
P
Vaultier
Michel
M
Iborra
José L
JL
D001709:Biotechnology / Q000379:methods; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D002849:Chromatography, Gas; D005656:Fungal Proteins; D006586:Hexanes / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry* / Q000494:pharmacology; D007477:Ions; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology; D013696:Temperature; D013997:Time Factors; D014867:Water / Q000737:chemistry
C493485:1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide; D005656:Fungal Proteins; D006586:Hexanes; D007093:Imidazoles; D007477:Ions; D010420:Pentanes; D013449:Sulfonamides; D014867:Water; C033353:pentane; D008049:Lipase; C431349:lipase B, Candida antarctica