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

Biomacromolecules
Ingrid Vikøren MoBjørn E Christensen

Abstract

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 f...Continue Reading

References

Mar 30, 1987·Biochemical and Biophysical Research Communications·D RobyA Toppan
Dec 2, 2010·Carbohydrate Research·Inga Unterieser, Petra Mischnick
May 14, 2011·Macromolecular Rapid Communications·Christophe Schatz, Sébastien Lecommandoux
Mar 21, 2012·Chemical Communications : Chem Comm·Ramon Novoa-Carballal, Axel H E Müller
Sep 16, 2014·Macromolecular Rapid Communications·Somasekhar BondalapatiAshraf Brik
Jan 17, 2015·Journal of Functional Biomaterials·Kazuo AzumaYoshiharu Okamoto
Jan 23, 2016·Chemical Reviews·Vinod K TiwariXi Chen
Oct 25, 2016·Chemistry : a European Journal·Oliver R BaudendistelValentin Wittmann
Sep 18, 2017·Carbohydrate Polymers·Ralph J Lehnert, Andreas Kandelbauer
Oct 4, 2017·Biomacromolecules·Benjamin B BreitenbachPeter R Wich
Jan 19, 2020·Carbohydrate Polymers·Ingrid Vikøren MoBjørn E Christensen
Mar 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maxence CoudurierStéphane Trombotto

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