Lipase-catalyzed synthesis and characterization of 1-butanoyl-2-palmitoyl phosphatidylcholine, a potential lipidic prodrug of butyric acid

1-Butanoyl-2-palmitoyl phosphatidylcholine was synthesized from dipalmitoylphosphatidylcholine (DPPC) and butyric acid using a lipase catalyzed transesterification in toluene at controlled water activity. A high fatty acid concentration and low water activity were essential for the enzymatic synthesis. The transesterification resulted in 97.3% incorporation of butyric acid in the sn-1 position with negligible incorporation in the sn-2-position. In mixtures with water, a liquid crystalline phase was formed in equilibrium with a micellar phase. The prepared phospholipid derivative could find applications as a lipidic anticancer prodrug of butyric acid.

► Synthesis is 1-butanoyl-2palmitoyl phosphatidylcholine (C4,C16-PC). ► Regioselective, lipase-catalyzed fatty acid exchange in phosphatidylcholine. ► Phase behavior of C4,C16-PC similar to that of lyso-PC. ► C4,C16-PC is a potential anticancer prodrug of butyric acid.