Synthesis of a fluorescent analogue of phosphatidylcholine.

A fluorescent analogue of phosphatidylcholine was synthesized by acylation of 1-oleoyl-sn-glycero-3-phosphocholine with 6-N-(tert-butyloxycarbonyl)aminocaproic acid anhydride employing the catalyst 4-pyrrolidinopyridine. Removal of the protective group by treatment with HCl in chloroform was followed by subsequent reaction with 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) to form the fluorescent analogue of phosphatidylcholine, 1-oleoyl-2-(NBD)aminocaproyl-sn-glycero-3-phosphocholine, in good yield and with high isomeric purity.