Lipidic peptides X. Synthesis, structural and physico-chemical elucidation of lipidic amino acid conjugates with hydrophilic compounds

Abstract

Lipidic amino acids 1a, c and dimer 1b were coupled to highly hydrophilic compounds, lactic, glycolic and gluconic acids and protected gulonic acid, yielding conjugates 1d,f,h,i,j,l and o. After carboxyl deprotection, acids e,g and m and were obtained. Physico-chemical investigations of these compounds were carried out using proton nuclear magnetic resonance. Plots of chemical shift versus concentration revealed the formation of aggregates or micelles at high concentrations and monomers at low concentrations.