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Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization

dc.rights.licenseopen
hal.structure.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorCOUDURIER, Maxence
hal.structure.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorFAIVRE, Jimmy
hal.structure.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorCRÉPET, Agnès
hal.structure.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorLADAVIÈRE, Catherine
hal.structure.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorDELAIR, Thierry
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.identifierIngénierie des Matériaux Polymères [IMP]
dc.contributor.authorTROMBOTTO, Stéphane
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2020
dc.identifier.issn1420-3049
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19701
dc.description.abstractEnThe nitrous acid depolymerization of chitosan enables the synthesis of singular chitosan oligosaccharides (COS) since their reducing-end unit is composed of 2,5-anhydro-d-mannofuranose (amf). In the present study, we describe a chemical method for the reducing-end conjugation of COS-amf by the commercially available dioxyamine O,O′-1,3-propanediylbishydroxylamine in high mass yields. The chemical structure of resulting dioxyamine-linked COS-amf synthesized by both oximation and reductive amination ways were fully characterized by 1H- and 13C-NMR spectroscopies and MALDI-TOF mass spectrometry. The coupling of chemically attractive linkers such as dioxyamines at the reducing end of COS-amf forms a relevant strategy for the development of advanced functional COS-based conjugates.
dc.description.sponsorshipMarquage non-covalent de siRNA par de petites séquences de copolymères à blocs pour une meilleure administration ciblée - ANR-16-CE09-0020
dc.language.isoen
dc.publisherMDPI
dc.rights.urihttp://creativecommons.org/licenses/by/
dc.subject.enchitosan
dc.subject.enoligomer
dc.subject.enreducing-end
dc.subject.enoxyamine
dc.subject.enbuilding-block
dc.subject.enconjugation
dc.title.enReducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization
dc.typeArticle de revue
dc.identifier.doi10.3390/molecules25051143
dc.subject.halChimie/Polymères
dc.subject.halChimie/Matériaux
dc.subject.halPhysique [physics]/Matière Condensée [cond-mat]/Matière Molle [cond-mat.soft]
bordeaux.journalMolecules
bordeaux.page1143
bordeaux.volume25
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue5
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-02530215
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-02530215v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Molecules&rft.date=2020&rft.volume=25&rft.issue=5&rft.spage=1143&rft.epage=1143&rft.eissn=1420-3049&rft.issn=1420-3049&rft.au=COUDURIER,%20Maxence&FAIVRE,%20Jimmy&CR%C3%89PET,%20Agn%C3%A8s&LADAVI%C3%88RE,%20Catherine&DELAIR,%20Thierry&rft.genre=article


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