Activation of enzymatically produced chitooligosaccharides by dioxyamines and dihydrazides
VIKØREN MO, Ingrid
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
FENG, Yiming
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
ØKSNES DALHEIM, Marianne
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
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Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
VIKØREN MO, Ingrid
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
FENG, Yiming
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
ØKSNES DALHEIM, Marianne
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
SOLBERG, Amalie
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
AACHMANN, Finn L.
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
SCHATZ, Christophe
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 3 LCPO : Polymer Self-Assembly & Life Sciences
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 3 LCPO : Polymer Self-Assembly & Life Sciences
CHRISTENSEN, Bjørn E.
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
< Reduce
Norwegian University of Science and Technology [Trondheim] [NTNU]
NOBIPOL, Department of Biotechnology and Food Science
Language
en
Article de revue
This item was published in
Carbohydrate Polymers. 2020, vol. 232, p. 115748
Elsevier
English Abstract
Reducing 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 ...Read more >
Reducing 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.Read less <
English Keywords
carbohydrates
chitosan
conjugation
hydrazides
oxyamines
Origin
Hal imported