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 13C 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 SO3/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.