Glycosylated cellulose derivatives with regioselective distributions of pendant glucose moieties

Abstract

Inspired by the presence of diverse carbohydrates on the surface of biological systems, we present herein a method for the synthesis of sugar-bearing polymers derived from renewable cellulose. In this paper, novel glycosylated cellulose derivatives were successfully synthesized containing a series of subsequent reactions: (1) synthesis of cellulose derivatives with pendant hydroxyl groups via nucleophilic substitution; (2) further sequential reactions containing a novel TEMPO/[bis(acetoxy)iodo]benzene (BAIB)-mediated oxidation of pendant hydroxyl groups, Schiff base formation and reduction in one-pot reaction; and (3) thiol-ene click reaction as an efficient tool to generate cellulose derivatives with pendant glucosyl groups. Furthermore, the glucosyl groups were only linked with the C6 position of anhydroglucose units (AGUs) of cellulose. Moreover, the glycosylated cellulose derivatives could be reversibly cross-linked by 1,4-phenylenediboronic acid at pH 10 and dissociated into single polymer chains by using glucose, which allow such glycolated cellulose derivatives to be interesting responsive materials.