Selective Reduction of Phosphatides with Lithium Aluminum Hydride. I. Ovolecithin

Abstract

The optimum conditions for cleavage of the fatty acid ester linkages in the lecithin molecule were found to be 20 min. at 10°C with the use of two moles of lithium aluminum hydride per mole of lecithin. The product formed under these conditions was identified to be l-α-glycerylphosphorylcholine when ovolecithin which was shown to be l-α-lecithin was used. Discussion has been presented as to two mechanisms possibly participating in the cleavage of glycerylphosphorylcholine, one involving a complex formation with the phosphoryl group and the other with the cationic nitrogen atom of the choline base.

L-α-(Dioleoyl)lecithin.* An Alternate Route to Its Synthesis

“…These attempts were unsuccessful. More recently, however, Urakami and Okura (1958) and Urakami et al (1960) have shown that if the deacylation of egg-yolk lecithin is carried out with lithium aluminum hydride an l--gly cerylphosphorylcholine is obtained which on reacylation yields optically pure L-a-lecithins. Material obtained by this method was used successfully by de Haas and van for the preparation of optically pure l-a-(dioleoyl)lecithin.…”