Lipoamino acid. Synthesis of amino acid esters of phosphatidyl glycerols.

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.