Water soluble trehalose-derived oligoamides

A new family of oligotrehaluronamides was synthesized through the polycondensation of alpha,alpha-trehaluronic acid dimethyl ester and different diamines or polyamines. In particular, diamines with different molecular structure (1,n-alkylene diamines, aromatic diamine, and alkyleneoxydiamine) were used in order to modulate the molecular weights and the physical characteristics of the products, such as T-g, hydrophilic or hydrophobic properties, and solubility. alpha,alpha-Trehaluronic acid was obtained from a renewable source as alpha,alpha-trehalose. The syntheses of oligotrehaluronamides were carried out in different solvents such as ethanol, methanol, THF and DMSO, using triethylamine as catalyst. All the compounds obtained in this study were characterized through FT-IR and NMR spectroscopy. The molecular weights were evaluated by H-1-NMR and in some cases compared with those obtained from ESI-MS spectrometry. Glass transition temperatures and melting points were detected by differential scanning calorimetry. Low molecular weight oligoamides, containing several hydroxyl groups, are water-soluble and could be used in water-based formulations.