An improved synthesis of 1-0-[3H] alkyl-2-acyl-sn-glycerol-3-phosphorylethanolamine with an unsaturated acyl chain.

A method is described for the synthesis of 1-0-[9', 10'-(3)H2] octadecyl-2-octadecenoyl-sn-glycerol-3-phosphorylethanol-amine, starting from rac 1-0-octadecen-9'-ylglycerol. The sn-1-alkyl enantiomer is obtained by an enzymatic reaction involving deacylation of rac 1-0-octadecen-9'-yl-2-octadecenoyl-glycerol-3-phosphoryl-N-(tert.-butyloxycarbonyl) ethanolamine with phospholipase A2. The resulting lyso compound is tritiated with 3H2 in the presence of platinum catalyst and reacylated with oleoyl anhydride to yield the final product.