Relative Lectin Binding Properties of T-Antigen-Containing Glycopolymers: Copolymerization ofN-Acryloylated T-Antigen Monomer vs. Graft Conjugation of Aminated T-Antigen Ligands onto Poly(N-acryloxysuccinimide)

Abstract

Water-soluble T-antigen- (Galβ(1–3)-GalNAcα) containing random glycopolymers were synthesized by two strategies: i) radical copolymerization of N-acryloylated monomers with (NH4)2S2O8 and ii) graft conjugation of an end-group-aminated T-antigen together with labeling reagent (16) by amidation onto poly(N-acryloxysuccinimide) and its derivatives followed by quenching with NH4OH. All glycoconjugates demonstrated antigenicity by double-radial immunodiffusion assays with peanut lectin from Arachis hypogaea. The biocytin-labeled terpolymer (23) also showed practical heterobifunctional antigenicity toward peanut lectin and streptavidin, giving the corresponding two precipitin bands in the assay.