Facile and high yielding syntheses of phosphatidylcholines and phosphatidylethanolamines containing 2H‐labeled acyl chains

Improved reliable methods for the partial chemical synthesis of phosphatidylcholines and phosphatidylethanolamines are described. Glycerophosphorylcholine (GPC) as its cadmium chloride complex was acylated rapidly (3 hr) with deuterated acyl anhydrides in dimethylformamide (DMF) to give phosphatidylcholines in > 90% yields. The products were free of sn‐1 and sn‐2 isomers. 2‐Lysophosphatidylcholines were rapidly acylated with acyl anhydrides, used in nearly stoichiometric amounts, in chloroform affording mixed‐chain phosphatidylcholines in > 85% yield. Pure phosphatidylethanolamines are prepared routinely in > 70% yield by an improved procedure from the corresponding phospatidylcholines using phospholipase‐D.