Polymeric water-soluble activated esters: synthesis of polymer backbones with pendant N-hydoxysulfosuccinimide esters for post-polymerization modification in water

Abstract

Novel polymer backbones with water-soluble activated ester pendant groups were synthesized by a reversible addition-fragmentation chain transfer (RAFT) polymerization technique using an acrylamide derivative bearing an N-hydroxysulfosuccinimide (sulfoNHS) ester as a monomer substrate. The monomer bearing a sulfoNHS ester was newly synthesized by a dehydrative condensation reaction of N-hydroxysulfosuccinimide sodium salt with 6-acrylamidohexanoic acid. The molecular weight and polydispersity indexes of the resulting polymers were well controlled by the RAFT polymerization mechanism. To synthesize glycopolymers, the substitution of the sulfoNHS esters on the polymer side chain with an amine-containing saccharide derivative, p-aminophenyl β-d-galactopyranoside (pAP-Gal), was performed in water. The resulting glycopolymer bearing pAP-Gals exhibited a strong interaction with the corresponding lectin peanut agglutinin in aqueous solution, because the saccharide moieties are multivalent. Novel polymer backbones with pendant water-soluble activated esters were synthesized by a reversible addition-fragmentation chain transfer (RAFT) polymerization technique using an acrylamide derivative bearing an N-hydroxysulfosuccinimide (sulfoNHS) ester as a monomer substrate. To synthesize glycopolymers, the substitution reaction at the sulfoNHS esters on the polymer side chain with an amine-containing saccharide derivative was performed in water. The resulting glycopolymer exhibited a strong interaction with the corresponding lectin in aqueous solution, because the saccharide moieties are multivalent.