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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Maxence CoudurierStéphane Trombotto

Abstract

The 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.

References

Aug 21, 2008·Angewandte Chemie·Jeet Kalia, Ronald T Raines
Nov 12, 2009·Chemical Communications : Chem Comm·Hongxue HuangXinmiao Liang
Jul 31, 2012·Carbohydrate Polymers·Alberto Maria MarzaioliCristina De Castro
Sep 12, 2013·Critical Reviews in Biotechnology·Subha Narayan DasAppa Rao Podile
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Jan 22, 2018·Carbohydrate Polymers·Fakhra Liaqat, Rengin Eltem
Jan 19, 2020·Carbohydrate Polymers·Ingrid Vikøren MoBjørn E Christensen

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Citations

Jun 12, 2021·Biopolymers·Camille ChapelleMyriam Desroches Le Foll

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Methods Mentioned

BETA
Nuclear Magnetic Resonance
NMR

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