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Activation of enzymatically produced chitooligosaccharides by dioxyamines and dihydrazides

dc.rights.licenseopen
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
dc.contributor.authorVIKØREN MO, Ingrid
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
dc.contributor.authorFENG, Yiming
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
dc.contributor.authorØKSNES DALHEIM, Marianne
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
dc.contributor.authorSOLBERG, Amalie
hal.structure.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
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.identifierNorwegian University of Science and Technology [Trondheim] [NTNU]
hal.structure.identifierNOBIPOL, Department of Biotechnology and Food Science
dc.contributor.authorCHRISTENSEN, Bjørn E.
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2020
dc.identifier.issn0144-8617
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19697
dc.description.abstractEnReducing end activation of poly-and oligosaccharides by bifunctional dioxyamines and dihydrazides enables aniline-free and cyanoborohydride-free conjugation to aldehyde-containing molecules, particles and surfaces without compromising the chain structure. Chitosans are due to their polycationic character, biodegradability, and bioactivity important candidates for conjugation. Here, we present a kinetic and structural study of the conjugation of a dioxyamine and a dihydrazide to enzymatically produced chitooligosaccharides ranging from N,N'-diacetylchitobiose to a decamer, all having N-acetyl D-glucosamine at the reducing end. Conjugation of the dioxyamine resulted in mixtures of (E)-and (Z)-oximes and β-N-pyranoside, whereas the dihydrazide yielded cyclic N-glycosides. Reaction kinetics was essentially independent of DP. Stable secondary amines were in both cases obtained by reduction with α-picoline borane, but higher temperatures were needed to obtain acceptable reduction rate. Comparison to dextran oligomers shows that the nature of the reducing end strongly influences the kinetics of both the conjugation and reduction.
dc.language.isoen
dc.publisherElsevier
dc.subject.encarbohydrates
dc.subject.enchitosan
dc.subject.enconjugation
dc.subject.enhydrazides
dc.subject.enoxyamines
dc.title.enActivation of enzymatically produced chitooligosaccharides by dioxyamines and dihydrazides
dc.typeArticle de revue
dc.identifier.doi10.1016/j.carbpol.2019.115748
dc.subject.halChimie/Polymères
dc.subject.halChimie/Matériaux
dc.subject.halPhysique [physics]/Matière Condensée [cond-mat]/Matière Molle [cond-mat.soft]
bordeaux.journalCarbohydrate Polymers
bordeaux.page115748
bordeaux.volume232
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-02530252
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-02530252v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Carbohydrate%20Polymers&rft.date=2020&rft.volume=232&rft.spage=115748&rft.epage=115748&rft.eissn=0144-8617&rft.issn=0144-8617&rft.au=VIK%C3%98REN%20MO,%20Ingrid&FENG,%20Yiming&%C3%98KSNES%20DALHEIM,%20Marianne&SOLBERG,%20Amalie&AACHMANN,%20Finn%20L.&rft.genre=article


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