Synthesis of Plasmenyl PC and PE Polar Lipids

Abstract

Plasmalogens are a type of polar lipid that are found naturally throughout the human body. These compounds are categorized as plasmalogens by a vinyl ether bond and an ester linked fatty acid chain. The plasmalogens in this study consist of the arachidonic, docosahexaenoic, and adrenic acid substituted species. Recent research has linked these plasmalogens to degenerative diseases which opens up their potential as biomarkers and new theraputics. This research synthesized each of these compounds in their glycerophosphoryl-ethanolamine (PE) and glycerophosphoryl-choline (PC) forms. Areas of this synthesis were explored, focusing on optimizing steps, success in the PC to PE conversion, and creating new plasmalogens. The PC to PE conversion step is notable because it uses an enzymatic reaction, transphosphatidylation, with phospholipase-D to cleave at the choline head and turn it into an ethanolamine head. This step was a concern with the low stability of the vinyl ether bond. This research proves this to be a promising method for the creation of these compounds.