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Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters

Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters

Journal of the American Oil Chemists' Society 73(11): 1481-1487

ISSN/ISBN: 0003-021X

DOI: 10.1007/bf02523514

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

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Accession: 002758220

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