Conversion of methylallyl alcohol into C2-methyl-1,2-di-O-hexadecylglycerophosphocholine, a conformationally restricted phospholipid.

The synthesis of C2-methyl-1,2-di-O-hexadecylglycerophosphocholine from methylallyl alcohol is described and the 13C-NMR assignments of all glycerol backbone and headgroup resonances are provided. Bond rotations in the glycerol backbone of this diether phospholipid derivative are impeded by steric hindrance exerted by the methyl group. We discuss the utility of this conformationally restricted C2-alkyl phospholipid analog for study of the influence of conformational changes at the lipid-water interface of bilayers on the interactions between lipids and other membrane components.