ENZYMATIC-SYNTHESIS OF MONOSACCHARIDE FATTY-ACID ESTERS AND THEIR COMPARISON WITH CONVENTIONAL PRODUCTS

5-O-Acyl-1,2-O-isopropylidene-D-xylofuranose and 6-O-acyl-1,2:3,4-di-O-isopropylidene-D-galactopyranose were enzymatically prepared from the corresponding monosaccharide acetals and commercial (crude) fatty acid mixtures. Subsequent acid-catalyzed hydrolysis of the isopropylidene group(s) gave monosaccharide esters with overall yields of 69-88%, where the monoester content was at least 80% (galactose oleate) and typically 90% for the other preparations. In contrast to sugar fatty acid esters prepared by conventional, high-temperature (trans)esterification, the enzymatically obtained monosaccharide esters contained no appreciable quantities of undesirable side products, and the only contaminants were monosaccharides and fatty acids.