Use of New Aminosugar Derivatives as Comonomers for the Synthesis of Glycosylated Poly(Amido-Amines)

Abstract

New sugar functionalized poly(amido-amines) (PAA) polymers were synthesized. The PAA made by the addition polymerization of 2-methylpiperazine-2,2-bisacrylamidoacetic acid (ISA) was chosen for its potential applications in the biomedical field and the sugar monomers were obtained by chemical and enzymatic synthetic strategies. Specifically, the 2-aminoethyl fi-D-galactopyranosyl monomer was directly obtained by enzymatic catalysis, while the 2-aminoethyl amide and the 3-aminopropyl amide of lactobionic acid were obtained by ning-opening reactions of the corresponding lactone. The presence of sugar moieties in the polymer chains was confirmed by FT-IR, 'H NMR, 1³C NMR analysis and calorimetric assay. The sugar content of polymer derivatives is sufficient for targeting purpose, making these compounds potential soluble drug carriers.