Molecular recognition capability and rheological behavior in solution of novel lactone-based glycopolymers

Novel glycopolymers have been prepared from ethylene–vinyl alcohol copolymers, EVOH. For that purpose, three distinct aminosaccharides (N-(4-aminobutyl)-d-gluconamide (NABG), N-(4-aminobutyl)-O-β-d-galactopyranosyl-(1 → 4)-d-gluconamide (NABL) and N-(4-aminobutyl)-O-β-d-glucopyranosyl-(1 → 4)-d-gluconamide (NABM) have been synthesized. The previous functionalization of these EVOH copolymers is mandatory to activate their hydroxyl reactivity before the subsequent coupling reaction with the aminosaccharides. The activation with carboxylic acid groups by reaction with phthalic anhydride has been chosen in the current investigation because of its almost quantitative yield and the subsequent high modification extent reached (>60%). The glycopolymers that turned out water-soluble (i.e., those based on NABL and NABM) have shown a reversible network formation unusually described in glycopolymers. In addition, their capability to interact with lectins, particularly Concanavalin A and Ricinus communis Agglutinin, has confirmed the specificity of lectin recognition in these glycopolymers.