Synthesis of phosphatidylcholine: an improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine.
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.
Ichihara
Ken'ichi
K
Biological Chemistry, Graduate School of Agricultural Science, Kyoto Prefectural University, Shimogamo, Kyoto 606-8522, Japan. ichihara@kpu.ac.jp
Iwasaki
Hitomi
H
Ueda
Kaori
K
Takizawa
Ryoko
R
Naito
Hideko
H
Tomosugi
Mitsuhiro
M
D015761:4-Aminopyridine / Q000031:analogs & derivatives / Q000737:chemistry; D000215:Acylation; D000818:Animals; D019256:Cadmium Chloride; D002384:Catalysis; D002845:Chromatography; D007692:Diatomaceous Earth; D004530:Egg Yolk / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry*; D005997:Glycerylphosphorylcholine / Q000737:chemistry*; D013058:Mass Spectrometry; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D010767:Phosphorylcholine / Q000737:chemistry*
D005227:Fatty Acids; D010713:Phosphatidylcholines; D010767:Phosphorylcholine; D005997:Glycerylphosphorylcholine; D007692:Diatomaceous Earth; D015761:4-Aminopyridine; D019256:Cadmium Chloride; C003885:4-dimethylaminopyridine