An efficient synthesis of phosphatidylcholines

This article deals with two of the major steps involved in phospholipid synthesis: the preparation of the optically pure precursors, sn-glycero-3-phosphocholine (GPC) and -ethanolamine, from a convenient lipid source such as egg yolk, and acylation of hydroxyl groups present in those precursors involving an acid to yield the corresponding phospholipid. Phosphatidylcholines and phosphatidylethanolamines were separated from lipids extracted from egg yolk using low-pressure column chromatography. The advantages of this method include the use of smaller volumes of solvents and silica gel and reuse of adsorbent. Acylation of GPC is aided by ultrasound from a common laboratory bath cleaner. Ultrasound-assisted base-catalyzed esterification of GPC is accomplished between 2-6 hours providing a phospholipid in more than 80% yield. This scheme is particularly valuable in the synthesis of polymerizable phospholipids.