Amphiphilic analogues of peptidoamines with perfluorinated side chains: Synthesis and preliminary investigations of their surfactant and complexing abilities

A new synthetic pathway for preparing perfluorinated β-alanines is described. 2-Perfluoroalkyl-ethanols are oxidized, dehydrofluorinated, substituted with an azide group and finally hydrogenated with excellent yields. The C-perfluoroalkylated β-alanines obtained in this way are subsequently used as hydrophobic moieties for the synthesis of amphiphilic lipo-peptides and lipo-peptidoamines. The choice of the peptidoamine structure is justified by the anti-oxidative and complexing properties of natural analogues such as carcinine and carnosine. Measurements of the surface tension of aqueous solutions of the compounds synthesized reveal their surfactant properties. Potentiometric and spectroscopic investigations give evidence for their good ability to complex copper(II) ions in solution.