Synthesis of new glycosaminoglycans-like families by regioselective oxidation followed by sulphation of glucoglucuronan from Rhizobium sp. T1

Glycosaminoglycan-like polysaccharides were prepared from Rhizobium sp. T1 polysaccharide using the TEMPO (nitroxyl radical 2,2,6,6-tetramethylpiperidine-1-oxyl radical) mediated oxidation. The structure of this new polyglucuronic acid sodium salt was analyzed by 13 C NMR spectra and HPAEC–PAD chromatography. Therefore, new polysaccharide containing only glucuronic acid monomers in both β -(1,3) and β -(1,4) linkage was obtained by the complete TEMPO-mediated oxidation of C6 primary hydroxyl groups of glucose of glucoglucuronan from Rhizobium sp. T1. Sulphation of this β -(1,3), β -(1,4)-polyglucuronic acid sodium salt was carried out using SO 3 /DMF reagent. These results suggested a new synthetic route using both TEMPO-mediated oxidation and sulphation of polysaccharides from Rhizobium sp. in developing glycosaminoglycans mimic to enhance the profitability of its low-cost production and processing industries. This novel carbohydrate derivative might find use as cheaper surrogates of glycosaminoglycans in the cosmetics and pharmaceutical fields.