Phospholipids. XVIII. Synthesis of ethylene glycolphosphonic acid analogues of cephalins

The synthesis of ethylene glycolphosphonic acid analogues of cephalins is reported. Two methods for the preparation of several typical members of the new type of phosphonolipids, viz. myristoyl, palmitoyl, and stearoyl ethylene glycol-(2-aminoethyl)phosphonate are described in detail The compounds were obtained by phosphonylation of monoacyl ethylene glycols in the presence of triethylamine with either (2-phthalimidoethyl)phosphonic acid monochloride or (2-N,N-dibenzylaminoethyl)phosphonic acid monochloride (hydrochloride), and freeing the reaction products from their protective groups by hydrazinolysis or hydrogenolysis, respectively. The glycolphosphonocephalins with long-chain fatty acid substituents, in contrast to the corresponding glycolphosphonolecithins, are water-insoluble, show no hemolytic activity, and are not hydrolyzed by lecithinase C to any significant degree. They are hydrolyzed, however, by lecithinase C in the presence of sphingomyelin.