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2,5-Anhydro-D-Mannose End-Functionalized Chitin Oligomers Activated by Dioxyamines or Dihydrazides as Precursors of Diblock Oligosaccharides

dc.rights.licenseopen
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
dc.contributor.authorMO, Ingrid Vikøren
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
dc.contributor.authorDALHEIM, Marianne Øksnes
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
dc.contributor.authorAACHMANN, Finn L.
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 3 LCPO : Polymer Self-Assembly & Life Sciences
dc.contributor.authorSCHATZ, Christophe
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
dc.contributor.authorCHRISTENSEN, Bjørn
dc.date.accessioned2020-11-24T09:53:10Z
dc.date.available2020-11-24T09:53:10Z
dc.date.issued2020-06-15
dc.identifier.issn1525-7797
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19631
dc.description.abstractEnDiblock 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.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.subject.enBiopolymers
dc.subject.enConjugate acid-base pairs
dc.subject.enBlock polysaccharides
dc.subject.enOxyamines
dc.subject.enDextran
dc.subject.enPolysaccharide chemical modification
dc.subject.enHydrazides
dc.subject.enChitin conjugation
dc.subject.enOligomers
dc.subject.enRedox reactions
dc.subject.enMolecular properties
dc.title.en2,5-Anhydro-D-Mannose End-Functionalized Chitin Oligomers Activated by Dioxyamines or Dihydrazides as Precursors of Diblock Oligosaccharides
dc.typeArticle de revue
dc.identifier.doi10.1021/acs.biomac.0c00620
dc.subject.halChimie/Polymères
dc.subject.halChimie/Matériaux
dc.subject.halPhysique [physics]/Matière Condensée [cond-mat]/Matière Molle [cond-mat.soft]
bordeaux.journalBiomacromolecules
bordeaux.page2884-2895
bordeaux.volume21
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue7
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-02894631
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-02894631v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Biomacromolecules&rft.date=2020-06-15&rft.volume=21&rft.issue=7&rft.spage=2884-2895&rft.epage=2884-2895&rft.eissn=1525-7797&rft.issn=1525-7797&rft.au=MO,%20Ingrid%20Vik%C3%B8ren&DALHEIM,%20Marianne%20%C3%98ksnes&AACHMANN,%20Finn%20L.&SCHATZ,%20Christophe&CHRISTENSEN,%20Bj%C3%B8rn&rft.genre=article


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