LIPOAMINO ACIDS: SYNTHESIS OF AMINO ACID ESTERS OF PHOSPHATIDYL GLYCEROLS
- 1 June 1966
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Biochemistry
- Vol. 44 (6) , 899-915
- https://doi.org/10.1139/o66-107
Abstract
The synthesis of α′-glycine and α′-alanine esters of α-(L-α-phosphatidyl)glycerols with myristic acid, palmitic acid, and stearic acid substituents is described. The lipoamino acids were obtained by the simultaneous phosphorylation of a D-α,β-diglyceride and azidoacyl β-benzyl glycerol with phenylphosphoryl dichloride and pyridine, isolation of the (diacyl L-α-glyceryl), (azidoacyl β-benzylglyceryl)-phenylphosphate by column chromatography on silicic acid, and the removal of the protective phenyl and benzyl groups as well as the reduction of the azido to the amino group in one operation by catalytic hydrogenolysis with a mixture of palladium and platinum catalysts.Azidoacetyl β-benzyl glycerol and 2-azidopropionyl β-benzyl glycerol were prepared by acylating β-benzyl glycerol with azidoacetyl chloride and 2-azidopropionyl chloride, respectively, and separating the mixtures of azidoacyl and bis-azidoacyl β-benzyl glycerols by column chromatography on silicic acid.Keywords
This publication has 17 references indexed in Scilit:
- Identification of a bacterial phospholipid as an O-ornithine ester of phosphatidyl glycerolBiochimica et Biophysica Acta, 1963
- Synthesis of L-α-(Dioleoyl)-cephalin; with a Comment on the Stereochemical Designation of Glycerolphosphatides1Journal of the American Chemical Society, 1959
- Possible Involvement of Lipids in Protein SynthesisScience, 1958
- Mono-α-aminoacyl and Mono-α-dipeptide TriglyceridesJournal of the American Chemical Society, 1955
- The Isolation of Dipalmitoleyl-L-α-glycerylphosphorylcholine from Yeast. A New Route to (Dipalmitoyl)-L-α-lecithin1Journal of the American Chemical Society, 1952
- Synthesis of Enantiomeric α-Cephalins1,2Journal of the American Chemical Society, 1952
- Synthesis of Enantiomeric α-Lecithins1Journal of the American Chemical Society, 1950
- 1,2,5,6-Diacetone d-Mannitol and 1,2,5,6-Diacetone l-MannitolJournal of the American Chemical Society, 1945
- Optically Active α,β-DiglyceridesJournal of the American Chemical Society, 1941
- XXVI.—The triazo-group. Part VIII. Azoimides of the monobasic aliphatic acidsJournal of the Chemical Society, Transactions, 1909