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Immobilization and enantioselectivity of Bacillus pumilus lipase in ionic liquids

Bustos-Jaimes, Ismael, García-Torres, Yareth, Santillán-Uribe, Hugo C., Montiel, Carmina
Journal of Molecular Catalysis. B, Enzymatic 2013 v.89 pp. 137-141
Bacillus pumilus, acetates, catalysts, catalytic activity, detergents, enantiomers, hexane, hexanoic acid, industrial applications, ionic liquids, laundry, silica gel, temperature, triacylglycerol lipase
Lipases are excellent catalysts for industrial applications ranging from laundry detergents to fine chemicals synthesis. Bacillus pumilus lipase A (BplA) belongs to a subfamily of small hydrolases displaying a remarkable enantioselectivity in hydrolytic reactions. Recombinant BplA was immobilized in silica gel and its enantioselectivity was evaluated. BplA displays a notorious enantioselectivity towards the R enantiomer of 1-phenylethyl acetate in hydrolytic reactions. In agreement with this hydrolytic enantioselectivity, BplA immobilized in silica gel is enantioselective towards the R enantiomer of 1-phenylethanol for the synthesis of its hexanoic acid ester in n-hexane as solvent. In contrast, isoinversion was observed in the ionic liquids 1-ethyl-3-methylimidazolium methanesulfonate ([Emim][CH3SO3]) or 1-ethyl-3-methylimidazolium methylsulfate ([Emim][EtSO4]). At temperatures from 25 to 35°C, BplA produces only the (R)-enantiomer of the ester, while at temperatures from 15 to 20°C the enantioselectivity is inverted towards the corresponding (S)-enantiomer.