Regioselective acylation of 1,6-anhydro-β-D-manno and galactopyranose catalysed by lipases

Article abstract of DOI:10.1016/0957-4166(95)00171-K

Pseudomonas fluorescens lipase (Amano) was found to be highly regioselective in the transesterification of 1,6-anhydro-β-D-manno and galactopyranose (mannosane and galactosane respectively) using vinyl acetate as an acyl donor.As in the case of 1,6-anhydro-β-D-glucopyranose (glucosane, the 4-OH axial group of mannosane is preferred, while the titled lipase catalysed the regioselective transesterification at the 2-axial OH of galactosane.The enzymatic acylation affords monoesters of the 1,6-anhydropyranoses which are difficult to obtain using conventional methods.