Enzymatic selective acylation of glycosides in ionic liquids: significantly enhanced reactivity and regioselectivity

Abstract

The enzymatic selective acylations of carbohydrates in ionic liquids were explored in both organic solvents and ionic liquids to see any significant differences in terms of reactivity and regioselectivity between two different classes of reaction media. Monoprotected glycosides (methyl-6-O-trityl-glucosides and galactosides) were chosen as the substrates with Candida rugosa lipase as an acylation enzyme. Two organic solvents, THF and chloroform, and two ionic liquids, [BMIM]+PF6- ([BMIM](+) = 1-butyl-3-methylimidazolium) and [MOEMIM]+PF6- ([MOEMIM](+) = 1-methoxyethyl-3-methylimidazolium), were employed as reaction media. The enzymatic reactions were performed in the presence of vinyl acetate at room temperature. It was observed that the reactions in ionic liquids took place more rapidly and more selectively than those in conventional organic solvents. (C) 2003 Elsevier B.V. All rights reserved.