Lipolytic synthesis of optically active 1,2-dibutyryl-sn-glycerol. Identification of diglyceride by solvent-dependent specific rotation

The objective was to determine whether the ini- tial pregastric lipase catalyzed hydrolysis of a triacylglycerol to 1,2(2,3)-diacylglycerol was a consequence of sn-specific hy- drolysis. The identity of the reaction products for the enzyme- assisted hydrolysis and uncatalyzed acyl-transfer reaction se- quence of tributyrylglycerol was assigned by 13 C nuclear mag- netic resonance. The optical activity of the product 1,2-dibutyryl-sn-glycerol (yield >50%, pH 6.5, 35°C, 13 min) was solvent dependent, being −2.92° (c ~1.3, CHCl 3 ) and +3.32° (c ~1.2, pyridine), and confirmation of sn-3 specificity by pregastric lipase was obtained. JAOCS 75, 1061-1062 (1998).