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.
D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010069:Oxadiazoles / Q000138:chemical synthesis*; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D010069:Oxadiazoles; D010713:Phosphatidylcholines; C047674:1-oleoyl-2-(7-(4-nitrobenzo-2-oxa-1,3-diazole))-6-aminocaproylphosphatidylcholine; D009327:4-Chloro-7-nitrobenzofurazan