Synthesis of Le x-neoglycoconjugate to study carbohydrate–carbohydrate associations and its intramolecular interaction

Abstract

A straightforward synthetic strategy for the preparation of the Le x neoglycoconjugate (11,11′-dithio bis[undecanyl-β- d-galactopyranosyl-(1→4)-α- l-fucopyranosyl-(1→3)-2-acetamido-2-deoxy-β- d-glucopyranoside]) and methyl Le x glycoside starting from the same trisaccharide donor is reported. This donor represents a very useful precursor for the construction of Le x derivatives. The Le x neoglycoconjugate has allowed the preparation of polyvalent gold glyconanoparticles and self-assembled monolayers on gold. 1H NMR of the Le x neoglycoconjugates suggests an intramolecular Le x–Le x cis-interaction in water, which is destroyed by addition of methanol.