“Click” synthesis of amphiphilic carbohydrate-alkyl triazole derivatives

Abstract

1,4-disubstituted 1H-1,2,3-triazole with a hydrophobic and hydrophilic moiety were synthesized by using Cu(I) catalyzed alkyne-azide 1,3-dipolar cycloaddition reaction. The hydrophilic moiety was D-galactopiranosyl or L-galactitoyl while an alkyl chain of eight to sixteen carbons corresponds to the hydrophobic portion. All compounds were characterized by NMR and mass spectrometry. Partition coefficient was experimentally determinate by HPLC ranging from 0.7 to 4.5. Compounds with the lowest partition coefficient showed self-aggregation in water leading to supramolecular structure, with size ranging from 108 to 588 nm.