SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

Abstract

A facile procedure for the preparation of saturated and unsaturated L-α-lecithins from L-α-glycerylphosphorylcholine (GPC) is reported. The lecithins are obtained by acylating L-α-GPC, in the form of its cadmium chloride addition compound, with fatty acid chloride and pyridine at low temperature (0°–25°). The acylation proceeds rapidly and yields optically pureL-α-lecithins. The preparation of the distearoyl-, dimyristoyl-, and dioleoyl L-α-lecithins by this procedure is described.The deacylation of lecithins with mercuric chloride or sodium hydroxide was investigated. Both procedures give a partially racemized L-α-GPC. This was established by the finding that the optical activity of the lecithins resulting from reacylating the L-α-GPC preparations in the form of their cadmium chloride compounds was considerably lower than that of the corresponding authentic lecithins.