Surface-Specific Cleavage of a Cationic Carbonate-Functionalized Vesicular Surfactant

摘要

A cationic, p-nitrophenyl carbonate functionalized 1,2-dipalmitoylglyceryl surfactant was synthesized. Vesicles created at pH 3.9 from this surfactant gave rapid partial p-nitrophenol release at pH 7.9, attributed to site-specific hydrolysis of exovesicular p-nitrophenyl carbonate moieties. Endovesicular p-nitrophenyl carbonates are cleaved approx. 700 times more slowly under these conditions, probably because they are protected by the maintenance of a pH gradient across the outer vesicle bilayer.