Journal of biological chemistry 228 no. 1:181-191




The synthesis of a phosphatidyl tripeptide has been accomplished. It was prepared by (a) phosphorylation of D-α,β-distearin with phenylphosphoryl dichloride and pyridine, (b) esterification of the resulting distearoylL- α-glycerylphenylphosphoryl chloride with N-carbobenzoxy-L-serylglycylglycine benzyl ester in the presence of lutidine, and (c) removal of the protective groups by catalytic hydrogenolysis. The O-( distearoyl-L-α-glycerylphosphoryl)- L-serylglycylglycine was obtained in an over-all yield of 12 per cent. The synthesis of N-carbobenzoxy-L-serylglycylglycine benzyl ester, for which two procedures have been reported, has been simplified considerably by condensing N -carbobenzoxy-L-serine with glycylglycine benzyl ester by means of N ,N' -dicyclohexylcarbodiimide. The phosphatidyl tripeptide is cleaved by diazomethane with the formation of the dimethyl ester of its phosphatidic acid moiety. This suggests that diazomethane may prove to be a valuable analytical tool in the elucidation of the structure of natural lipopeptides and lipoproteins

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