Synthesis of phosphatidylcholine: an improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine

Chem Phys Lipids. 2005 Oct;137(1-2):94-9. doi: 10.1016/j.chemphyslip.2005.06.001.

Abstract

An improved safe method that does not contaminate the environment with cadmium chloride, a toxic heavy metal salt, was developed for the synthesis of phosphatidylcholine (PC). PC was synthesized from sn-glycero-3-phosphocholine (GPC) and fatty acid in one step under mild conditions without the use of cadmium chloride. GPC was prepared from egg yolk PC and adsorbed by kieselguhr in a Teflon vessel. The GPC on kieselguhr was acylated with fatty acid in the presence of two reagents, dicyclohexylcarbodiimide for synthesis of fatty acid anhydride and 4-dimethylaminopyridine as an acylating catalyst, at 30 degrees C overnight. The PC thus produced was purified by silica gel column chromatography. The yield of dioleoyl PC was 90% based on the starting material, GPC.

MeSH terms

  • 4-Aminopyridine / analogs & derivatives
  • 4-Aminopyridine / chemistry
  • Acylation
  • Animals
  • Cadmium Chloride
  • Catalysis
  • Chromatography
  • Diatomaceous Earth
  • Egg Yolk / chemistry
  • Fatty Acids / chemistry*
  • Glycerylphosphorylcholine / chemistry*
  • Mass Spectrometry
  • Phosphatidylcholines / chemical synthesis*
  • Phosphorylcholine / chemistry*

Substances

  • Fatty Acids
  • Phosphatidylcholines
  • Phosphorylcholine
  • Glycerylphosphorylcholine
  • Diatomaceous Earth
  • 4-Aminopyridine
  • Cadmium Chloride
  • 4-dimethylaminopyridine