Synthesis of Polar Head Group Homologs of All-Trans-Cyclopentano-Phosphatidylcholine, phosphatidyl-N,N-dimethylethanolamine, and Phosphatidylethanolamine

J Lipid Res. 1984 Mar;25(3):294-303.

Abstract

The polar head group region of a conformationally restricted analog of phosphatidic acid (diacylglycero-phosphate) has been systematically modified to give analogs of phosphatidylcholine, phosphatidylethanolamine, and phosphatidyl-N,N-dimethylethanolamine. These analogs differ from their natural counterpart in both the backbone region and in the polar head region, respectively, as follows: the diacylglyceryl moiety has been replaced by an all-trans diacylcyclopentane-1,2,3-triol moiety and the phosphorus-nitrogen separation has been increased incrementally from two to nine methylene units. The synthesis of these homologous series involved phosphorylation of (1,3/2)-2,3-dipalmitoylcyclopentane-1,2,3-triol with each of a series of homologous bromoalkylphosphoric acid dichlorides, which were themselves obtained by phosphorus oxychloride treatment of the homologous bromoalkanols. The resulting bromoalkyl esters of 2,3-dipalmitoylcyclopentane-1,2,3-triol-1-phosphoric acid were reacted with trimethylamine, dimethylamine, or ammonia to give the cyclopentano-phosphatidylcholines, cyclopentano-N,N-dimethylethanolamines, and cyclopentano-phosphatidylethanolamine, respectively. All the compounds were obtained as stable microcrystalline solids. The yields of cyclopentano-phosphatidylethanolamines and of cyclopentano-N,N-dimethylethanolamines were reduced by the formation of compounds which analyzed as monoacyl (lyso) derivatives.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Chromatography, Thin Layer
  • Cyclopentanes
  • Indicators and Reagents
  • Phosphatidylcholines / chemical synthesis*
  • Phosphatidylethanolamines / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Cyclopentanes
  • Indicators and Reagents
  • Phosphatidylcholines
  • Phosphatidylethanolamines
  • phosphatidyldimethylethanolamine