APPLICATION OF LIPASES TO THE REGIOSELECTIVE SYNTHESIS OF SUCROSE FATTY-ACID MONOESTERS

A regioselective synthesis of 6'-O-acyl sucrose monoesters has been de veloped through the lipase-catalyzed esterification of sucrose acetals with fatty acids in both organic solvents and under solvent-free cond itions. The products were obtained in overall yields of 20-27% after h ydrolysis of the isopropylidene groups with aqueous acids. The strict selectivity of the enzymes used also enabled the preparation of a mono ester fraction that was highly enriched in 6-O-acyl sucrose. This was accomplished by lipase-catalyzed transesterification of sucrose monoes ters, prepared by conventional chemical methods, in propan-2-ol. After removal of the transesterification products (sucrose and fatty acid i sopropyl esters) and column chromatography on silica gel, the obtained monoester product contained 80% of the single regioisomer, 6-O-acyl s ucrose.