SYNTHESIS OF PHOSPHOLIPID ANALOGS - VARIATION OF THE P-N DISTANCE

Phosphatidyl choline analogues with increased phosphate-trimethylammonium distance and phosphatidyl ethanolamine analogues with increased phosphate-ammonium distance were synthesised. The distance was varied by the incorporation of additional methylene groups, from 2 (natural) to 11 CH2-units. The synthesis of the analogues was possible by phosphorylation of 1,2-dipalmitoyl-sn-glycerol with bromoalkylphosphoric acid dichlorides which were obtained from the respective bromoalkanols and phosphorus oxychloride. The resulting bromoalkylesters of 1,2-dipalmitoyl-sn-glycerol were subjected to direct amination with trimethylamine, dimethylamine, methylamine and ammonia to yield the respective phosphatidyl choline and ethanolamine analogues. Chromatographically pure products were obtained in yields of 50 to 70% of the 1,2-diacyl glycerol. © 1979.