Design, Synthesis, and Self-Assembly of an Ether and Amide Linkage-Based Cyclic Lipid

A novel 48-membered cyclic lipid, in which two ether and two amide groups serve as a linker between its hydrophilic and hydrophobic moiety, was synthesized starting from D-1,2-O-isopropylidene-sn-glycerol. The synthetic scheme is featured by the selective removal of protecting groups, followed by the introduction of mesylate and carboxylic acid, which sequentially leads to the formation of ether and amide bonds, respectively. Transmission electron microscopic observation confirmed that this lipid forms submicrosized helical ribbons.