Enzymatic synthesis of structured 1,2-diacyl-sn-glycerol-3-phosphocholines from glycerol-sn-3-phosphocholine.

摘要

Synthesis of structured 1,2-diacyl-sn-glycero-3-phosphocholines (sn-1,2-PC) from glycerol-sn-3-phosphocholine (GPC) was studied by means of enzymic acylation reactions of the 2 free sn- positions of the glycerol backbone. After 22 h, high conversions (absolute yields = 100%) of GPC to sn-2-lysophosphatidylcholines (sn-2-LPC) were achieved using Novozym 435, a lipase from Candida antarctica, selective for the sn-1-position of GPC. In the 2nd step, acylation of the sn-2-position of the sn-2-LPC was catalysed using phospholipase A2 from swine pancreas and better acylation yields (40% absolute yield, corresponding to a relative yield of 70% when reactions were carried out at controlled aw) were obtained compared to analogous reactions reported in the literature. A chemical procedure to obtain structured sn-1,2-PC from sn-2-LPC was also used and better results (65% absolute yield, corresponding to a relative yield of 95%) were obtained in comparison with the enzymic method.