Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

Abstract

The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F(2t)-isoprostane and ent-15-epi-F(2t)-isoprostane has allowed for the selective preparation of 15-F(2t)-isoprostanyl phosphatidylethanolamine and ent-15-epi-F(2t)-isoprostanyl phosphatidylcholine. The nature of the headgroups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary 1H NMR and 31P NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.