title: Preparation and NMR characterization of glucosamine oligomers bearing an azide function using chitosan.
abstract: In this study, a procedure to produce glucosamine oligomers with the amino functions transformed into azido groups was optimized, and HPLC purification afforded to the isolation of nine different oligosaccharides derivatives, with the reducing end transformed in alditol. These oligomers differed for the degree of polymerization and for the type of alditol at the reducing end. The first group comprehended species from di- to hexasaccharide, with all the amino functions converted into an azido group. The second and the third groups were isolated in minor yields, and were both constituted from tri- and tetrasaccharides; the difference between the two groups regarded exclusively the type of alditol found at the reducing end, which was a glucosaminitol in the first case, or a N-acetylglucosaminitol in the other. Products were fully characterized by 2D NMR spectroscopy. The azido moieties installed on these oligosaccharides can be further exploited in Cu(I) catalyzed azido-alkyne cycloaddition reactions.
authors: Università di Napoli Federico II, Dipartimento di Scienze Chimiche, Complesso Universitario Monte Sant'Angelo, Via Cintia 4, 80126 Napoli, Italy.
authors: Alberto
authors: A
authors: Maria Marzaioli
authors: Emiliano
authors: E
authors: Bedini
authors: Rosa
authors: R
authors: Lanzetta
authors: Vincenzo
authors: V
authors: Perino
authors: Michelangelo
authors: M
authors: Parrilli
authors: Cristina
authors: C
authors: De Castro
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002240:Carbohydrate Sequence; D002384:Catalysis; D048271:Chitosan / Q000494:pharmacology*; D005944:Glucosamine / Q000138:chemical synthesis / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D001386:Azides; D009844:Oligosaccharides; D011108:Polymers; D048271:Chitosan; D005944:Glucosamine