2,5-Anhydro-D-Mannose End-Functionalized Chitin Oligomers Activated by Dioxyamines or Dihydrazides as Precursors of Diblock Oligosaccharides
| Autor: | Marianne Øksnes Dalheim, Christophe Schatz, Bjørn E. Christensen, Finn Lillelund Aachmann, Ingrid Vikøren Mo |
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| Přispěvatelé: | NOBIPOL, Department of Biotechnology and Food Science, Norwegian University of Science and Technology [Trondheim] (NTNU), Norwegian University of Science and Technology (NTNU)-Norwegian University of Science and Technology (NTNU), Norwegian University of Science and Technology (NTNU), Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC), Team 3 LCPO : Polymer Self-Assembly & Life Sciences, Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Polymers and Plastics
Mannose Oligosaccharides Bioengineering Chitin 02 engineering and technology macromolecular substances Borane 010402 general chemistry Hydrazide Polysaccharide 01 natural sciences Redox Oxyamines Article Biomaterials chemistry.chemical_compound Residue (chemistry) Biopolymers Materials Chemistry Redox reactions Dextran chemistry.chemical_classification Chitin conjugation Conjugate acid-base pairs Depolymerization Chemistry Block polysaccharides [CHIM.MATE]Chemical Sciences/Material chemistry 021001 nanoscience & nanotechnology Hydrazides Molecular properties Combinatorial chemistry 0104 chemical sciences carbohydrates (lipids) [CHIM.POLY]Chemical Sciences/Polymers Oligomers Polysaccharide chemical modification 0210 nano-technology [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft] |
| Zdroj: | Biomacromolecules Biomacromolecules, American Chemical Society, 2020, 21 (7), pp.2884-2895. ⟨10.1021/acs.biomac.0c00620⟩ |
| ISSN: | 1525-7797 1526-4602 |
| Popis: | International audience; Diblock oligosaccharides based on renewable resources allow for a range of new but, so far, little explored biomaterials. Coupling of blocks through their reducing ends ensures retention of many of their intrinsic properties that otherwise are perturbed in classical lateral modifications. Chitin is an abundant, biodegradable, bioactive, and self-assembling polysaccharide. However, most coupling protocols relevant for chitin blocks have shortcomings. Here we exploit the highly reactive 2,5-anhydro-D-mannose residue at the reducing end of chitin oligomers obtained by nitrous acid depolymerization. Subsequent activation by dihydrazides or dioxyamines provides precursors for chitin-based diblock oligosaccharides. These reactions are much faster than for other carbohydrates, and only acyclic imines (hydrazones or oximes) are formed (no cyclic N-glycosides). α-Picoline borane and cyanoborohydride are effective reductants of imines, but in contrast to most other carbohydrates, they are not selective for the imines in the present case. This could be circumvented by a simple two-step procedure. Attachment of a second block to hydrazide- or aminooxy-functionalized chitin oligomers turned out to be even faster than the attachment of the first block. The study provides simple protocols for the preparation of chitin-b-chitin and chitin-b-dextran diblock oligosaccharides without involving protection/deprotection strategies. |
| Databáze: | OpenAIRE |
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