Convenient synthesis of racemic mixed-chain ether glycerophosphocholines from fatty alkyl allyl ethers: useful analogs for biophysical studies.
Diether glycerophosphocholines containing one long and one short chain were synthesized in moderate yield. The synthesis of a diether glycerophosphocholine containing a branched chain and a straight chain is also described. Alkylation of fatty alcohol with allyl bromide and dimethyl sulfoxide anion gave fatty alkyl allyl ether, which was hydroxylated and tritylated. By procedures described previously, 1-O-alkyl-3-O-triphenyl-methylglycerol was alkylated, detritylated, and converted into the phosphocholine product. This method is of general utility for the preparation of a variety of mixed-chain racemic glycerophosphocholines whose physical properties are of interest in studies of biological membranes.
D000498:Allyl Compounds; D055592:Biophysical Phenomena; D001703:Biophysics; D055598:Chemical Phenomena; D002621:Chemistry; D004987:Ethers; D005227:Fatty Acids; D005997:Glycerylphosphorylcholine; D008722:Methods; D010713:Phosphatidylcholines / Q000138:chemical synthesis*
D000498:Allyl Compounds; D004987:Ethers; D005227:Fatty Acids; D010713:Phosphatidylcholines; D005997:Glycerylphosphorylcholine