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Volume 25
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Communication

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

by
Maxence Coudurier
1,
Jimmy Faivre
1,
Agnès Crépet
1,
Catherine Ladavière
1,
Thierry Delair
1,
Christophe Schatz
2 and
Stéphane Trombotto
1,*
1
Ingénierie des Matériaux Polymères, IMP UMR CNRS 5223, Univ Lyon, Université Claude Bernard Lyon 1, F-69622 Villeurbanne, France
2
Laboratoire de Chimie des Polymères Organiques (LCPO), Univ Bordeaux, CNRS, Bordeaux INP, UMR 5629, F-33600 Pessac, France
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(5), 1143; https://doi.org/10.3390/molecules25051143
Submission received: 4 February 2020 / Revised: 25 February 2020 / Accepted: 1 March 2020 / Published: 4 March 2020
(This article belongs to the Section Macromolecular Chemistry)
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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.
Keywords: chitosan; oligomer; reducing-end; conjugation; building-block; oxyamine chitosan; oligomer; reducing-end; conjugation; building-block; oxyamine
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MDPI and ACS Style

Coudurier, M.; Faivre, J.; Crépet, A.; Ladavière, C.; Delair, T.; Schatz, C.; Trombotto, S. Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization. Molecules 2020, 25, 1143. https://doi.org/10.3390/molecules25051143

AMA Style

Coudurier M, Faivre J, Crépet A, Ladavière C, Delair T, Schatz C, Trombotto S. Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization. Molecules. 2020; 25(5):1143. https://doi.org/10.3390/molecules25051143

Chicago/Turabian Style

Coudurier, Maxence, Jimmy Faivre, Agnès Crépet, Catherine Ladavière, Thierry Delair, Christophe Schatz, and Stéphane Trombotto. 2020. "Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization" Molecules 25, no. 5: 1143. https://doi.org/10.3390/molecules25051143

APA Style

Coudurier, M., Faivre, J., Crépet, A., Ladavière, C., Delair, T., Schatz, C., & Trombotto, S. (2020). Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization. Molecules, 25(5), 1143. https://doi.org/10.3390/molecules25051143

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