Regioselectivity of Lipase-Catalysed Deacetylation of Methyl 2,3,5-tri-OAcetyl-α, β-D-Furanosides in Ionic Liquid
Esteban D. Gudino,
Adolfo M. Iribarren,
Luis E. Iglesias.
Ionic liquids (ILs) were assayed as reaction medium for the enzymatic deacetylation of three methyl 2,3,5-tri- O-acetyl-α,β-D-furanosides and the obtained results show the influence of the IL and the furanose structure on the regioselectivity of hydrolyses catalysed by the tested lipases. In a reaction medium consisting of a 1:1 mixture of 30 mM phosphate buffer (pH 7) and 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]), Candida rugosa lipase catalysed the formation of methyl 2,3-di-O-acetyl-α,β-D-arabinofuranoside in 77 %, while in a 9:1 mixture of the same buffer and 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4]), methyl 2,3-di-O-acetyl-α,β-D-ribofuranoside was obtained in 62 %.
Keywords: Furanoses, furanosides, ionic liquids, lipases, Candida antarctica lipase B, Candida rugosa lipase, regioselectivity, acylated carbohydrates, natural products analogs, nucleosides, biocatalysis, regioselectively, carbohydrates, alcoholysis, Enzymatic Hydrolysis
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