Synthesis and polymerization of new styryl and methacryloyl monomers containing acidic saccharide moieties

Abstract

New styryl-type water-insoluble and methacryloyl-type water-soluble monomers, N-(p-vinylbenzyl)-1,2-O-isopropylidene-6-D-glucofuranuronamide and N-(2methacryloylamino)ethyl-1,2-O-isopropylidene-6-D-glucofuranuronamide, were synthesized from the most common acidic saccharide, D-glucuronic acid. Their radical homopolymerizations and copolymerizations with styrene and acrylamide were tried under various conditions. The isopropylidene groups in the resulting polymers were removed in a mixture of trifluoroacetic acid and water (2/1 v/v) to give the corresponding polymers with many pendant D-glucopyranuronyl groups with reactive reducing groups. The pendant reducing ends may be useful as potential binding sites under a hydrophilic atmosphere.