Synthesis of lysophosphoglycerides

Abstract

The chemical syntheses of 2-stearoyl-glycerol-1-phosphorylcholine, 2-[9,10–3H]-stearoyl- glycerol-3-phosphorylcholine, (rac)-1- and 2-stearoyl-glycerol-3-phosphorylcholine, (rac)-1- and 2-stearoyl-glycerol-3-phosphoryl-(N,N-dimethyl)ethanolamine and (rac)-1- and 2-stearoyl-glycerol-3-phosphate are described. These lysophosphoglycerides were prepared using (rac)-isomeric-0-benzyl-stearoyl-glycerol-3-(benzyl)phosphates as starting products. Hydrogenolysis of this latter compounds yielded the lysophosphatidic acids while reaction of the silver salts of the starting products with 2-bromo-ethyl N,N-dimethylamine picrate or 2-bromo-ethyl trimethylammonium picrate finally led to the isomeric N,N-dimethyl lysophosphatidyl ethanolamines and lysolecithins respectively. The (rac)-isomeric-0- benzyl-stearoyl-glycerol-3-phosphoryl-(N,N-dimethyl)ethanolamines could easily be converted with methyl iodide into the corresponding lecithins. Stereospecific degradation of (rac)-1-0-benzyl-2-stearoyl-glycerol-3-phosphorylcholine with phospholipase A (EC 3.1.1.4) gave 1-0-benzyl-glycerol-3-phosphorylcholine leaving 3-0-benzyl-2-stearoyl- glycerol-1-phosphorylcholine unhydrolysed. The latter product yielded upon hydrogen-olysis 2-stearoyl-glycerol-1-phosphorylcholine. The first product viz. 1-0-benzyl-glycerol- 3-phosphorylcholine was acylated with [9,10–3H]-stearoyl chloride and after removal of the protecting benzyl group 2-[9,10–3H]-stearoyl-lysolecithin was obtained.

Infrared spectra of the synthesized lysophosphoglycerides are reported. Some general properties of the lyso compounds e.g. their behaviour towards phospholipase A and their stability are discussed.