Document Type
Article
Disciplines
Biochemistry
Abstract
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
Article Number
1040
Publication Date
1957
Recommended Citation
Baer, Erich; Maurukas, Jonas; and Clarke, Donald Dudley PhD, "Synthesis of phosphatidyl peptides I. o-(distearoyl-l-a-glycerylphosphoryl)-l-serylglycylglycine / by Erich Baer, Jonas Maurukas, and Donald D. Clarke (From the Banting and Best Department of Medical Research, University of Toronto, Toronto, Canada)" (1957). Chemistry Faculty Publications. 41.
https://research.library.fordham.edu/chem_facultypubs/41
Comments
Journal of biological chemistry 228 no. 1:181-191