Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis

1,3-Oleoyl-2-palmitoylglycerol (OPO), an important structured triglyceride in infant nutrition, was synthesized by a two-step process in high yields a nd purity using sn1,3-regiospecific lipases. in the first step, tripalmitin (TP) was subjected to an alcoholysis reaction in an organic solvent cataly zed by sn1,3-regiospecific lipases yielding the corresponding 2-monopalmiti n (2-MP). The 2-MP was isolated in up to 85% yield and >95% purity by cryst allization and esterified in the second step with oleic acid using the same lipases to form the structured triglyceride OPO in up to 78% yield contain ing 96% palmitic acid in the sn2-position. Water activity, solvent, as well as carrier for lipase immobilization strongly influenced the yield and pur ity of products in both steps. The best results were achieved with lipases from Rhizomucor miehei and Rhizopus delemar immobilized on EP 100 and equil ibrated to a water activity of 0.43. Special emphasis was given to develop this process in solvents that are allowed to be used in foodstuffs and to p erform the second step in a solvent-free system. (C) 1999 John Wiley & Sons . Inc.