Synthesis of phosphatidylcholine under possible primitive earth conditions.
Using a primitive Earth evaporating pond model, the synthesis of phosphatidylcholine was accomplished when a reaction mixture of choline chloride and disodium phosphatidate, in the presence of cyanamide and traces of acid, was evaporated and heated at temperatures ranging from 25 degrees to 100 degrees C for 7 hours. Optimum yields of about 15% were obtained at 80 degrees C. Phosphatidylcholine was identified by chromatographic, chemical and enzymatic degradation methods. On enzymatic hydrolysis with phospholipase A2 and phospholipase C, lysophosphatidylcholine and phosphorylcholine were formed, respectively. Alkaline hydrolysis gave glycerophosphorylcholine. The synthesis of phosphatidylcholine as the major compound was accompanied by the formation of lysophosphatidylcholine in smaller amounts. Cyanamide was found to be essential for the formation of phosphatidylcholine, and only traces of HCl, of the order of that required to convert the disodium phosphatidate to free phosphatidic acid were found necessary for the synthesis. This work suggests that phosphatidylcholine, which is an essential component of most biological membranes, could have been synthesized on the primitive Earth.
D002794:Choline; D006851:Hydrochloric Acid; D007700:Kinetics; D010713:Phosphatidylcholines / Q000138:chemical synthesis; D010741:Phospholipases A; D054467:Phospholipases A2; D013696:Temperature; D010738:Type C Phospholipases
D010713:Phosphatidylcholines; D010741:Phospholipases A; D054467:Phospholipases A2; D010738:Type C Phospholipases; D002794:Choline; D006851:Hydrochloric Acid