title: Synthesis of new glycosaminoglycans-like families by regioselective oxidation followed by sulphation of glucoglucuronan from Rhizobium sp. T1.
abstract: 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 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.
authors.affiliation: LPMV, Université de Picardie Jules Verne, Avenue des Facultés, Le Bailly, F-80025 Amiens Cedex 1, France.
authors.forename: Elboutachfaiti
authors.initials: E
authors.lastname: Redouan
authors.affiliation: LPMV, Université de Picardie Jules Verne, Avenue des Facultés, Le Bailly, F-80025 Amiens Cedex 1, France.
authors.forename: Petit
authors.initials: P
authors.lastname: Emmanuel
authors.affiliation: Laboratoire de Génie Chimique et Biochimique, Université Blaise Pascal Polytech Clermont Ferrand, 24 Avenue des Landais, 63174 Aubière Cedex, France.
authors.forename: Michaud
authors.initials: M
authors.lastname: Philippe
authors.affiliation: LPMV, Université de Picardie Jules Verne, Avenue des Facultés, Le Bailly, F-80025 Amiens Cedex 1, France.
authors.forename: Courtois
authors.initials: C
authors.lastname: Bernard
authors.affiliation: LPMV, Université de Picardie Jules Verne, Avenue des Facultés, Le Bailly, F-80025 Amiens Cedex 1, France.
authors.forename: Courtois
authors.initials: C
authors.lastname: Josiane
authors.affiliation: GREENTECH Biotechnologies, Biopôle Clermont Limagne, 63360 Saint Beauzire, France.
authors.forename: Delattre
authors.initials: D
authors.lastname: Cedric
mesh_terms: D002236:Carbohydrate Conformation; D006025:Glycosaminoglycans / Q000096:biosynthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012231:Rhizobium / Q000378:metabolism*
chemical_list: D006025:Glycosaminoglycans; C020341:glucosaminoglycans