Novel xylylene diaminocellulose derivatives for enzyme immobilization

Abstract

In the series of soluble and film-forming aminocelluloses for application as enzyme-compatible support matrices, novel derivatives with xylylene diamine residues selectively at C6 and solubilizing carbanilate groups were synthesized. Synthesis of these aminocelluloses was successful in three reaction steps starting from cellulose (Avicel PH 101) via tosylcellulose with degree of substitution of 0.88 (preferably at C6) and tosylcellulose carbanilate. Using a 10-fold excess of xylylene diamine, only one amino group of the diamine reacts during the nucleophilic substitution of the tosylate groups. In the last step, the influence of the structure of the starting xylylene diamine isomers and of the reaction conditions on the degree of substitution of the tosylate, carbanilate and xylylene diamino groups in the final polymer, on the occurrence of side reactions and on the polymer solubility was studied. All xylylene diamino tosylcellulose carbanilates are soluble in DMA, DMSO and DMF in never dried state and form transparent films on glass surfaces. These films are promising support matrices for enzyme immobilization because of their characteristic topography, as is shown by atomic force microscopy examinations of the film surfaces.