Enzymatic synthesis of monosaccharide fatty acid esters and their comparison with conventional products

Abstract

Abstract 5‐ O ‐Acyl‐1,2‐ O ‐isopropylidene‐D‐xylofuranose and 6‐ O ‐acyl1,2∶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 59–88%, 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 undersirable side products, and the only contaminants were monosaccharides and fatty acids.