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Dextrin is a polymer composed of α-(1→4) d-glucose units produced by partial hydrolysis of starch. In this work, the transesterification of the soluble polysaccharide with vinyl acrylate (VA) was carried out in anhydrous dimethylsulfoxide (DMSO). The effect of the water activity and of the enzyme Proleather, on the reaction rates, was analysed. Different degrees of substitution (DS) ranging from ca. 10% to 70% were obtained by controlling the molar ratio of VA to dextrin. Gels were obtained by free radical polymerization of dextrin-VA, with different degrees of substitution and monomer concentration, in water. A comprehensive solid state-NMR analysis of the hydrogels was performed. These hydrogels are being developed as scaffold materials for bioactive molecule and cell delivery, tissue engineering and a variety of other biomedical applications.