Preparation and NMR characterization of glucosamine oligomers bearing an azide function using chitosan
| Autor: | Alberto M. Marzaioli, Emiliano Bedini, Vincenzo Perino, Cristina De Castro, Michelangelo Parrilli, Rosa Lanzetta |
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| Přispěvatelé: | Alberto Maria, Marzaioli, Bedini, Emiliano, Lanzetta, Rosa, Perino, VINCENZO ROMILDO, Parrilli, Michelangelo, DE CASTRO, Cristina |
| Rok vydání: | 2012 |
| Předmět: |
Azides
Chitosan Glucosamine Magnetic Resonance Spectroscopy Polymers and Plastics Polymers Hydrolysis Organic Chemistry Oligosaccharides Degree of polymerization Models Biological High-performance liquid chromatography Catalysis Cycloaddition chemistry.chemical_compound Carbohydrate Sequence chemistry Materials Chemistry Organic chemistry Azide Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Carbohydrate Polymers. 90:847-852 |
| ISSN: | 0144-8617 |
| DOI: | 10.1016/j.carbpol.2012.06.010 |
| Popis: | 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) catalysed azido-alkyne cycloaddition reactions. |
| Databáze: | OpenAIRE |
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