Esterification of Glycosides with Glycerol and Trimethylolpropane Moieties by Candida cylidracea Lipase.

Abstract

Glycosides, the reducing ends of which were glycerol and 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (trimethylolpropane, TMP), were esterified with oleic acid (OA) by a lipase from Candida cylindracea. Two glycosides, 1-O-β-d-galactosyl glycerol (Gal-1-Gl) and O-β-d-glucosyl TMP (Glc-TMP), were enzymatically synthesized by transglycosylation. GIc-TMP was esterified at a higher water content than Gal-1-Gl. When an equal amount of the glycosides and OA were used as substrates, almost 20% and 50% of OA were consumed for the esterification of Gal-1-Gl and Glc-TMP, respectively. Laurie, capric, and caprylic acids also gave esters. Oleic ester synthesis was compared among several related glycosides. The enzyme esterified the glycosides with a TMP moiety better than those with a glycerol moiety. The reaction was scarcely affected not only by the kind of monosaccharide moieties but also by anomeric linkage types between the moieties.