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

Maxence Coudurier (1) , Jimmy Faivre (1) , Agnès Crépet (1) , Catherine Ladavière (1) , Thierry Delair (1) , Christophe Schatz (2, 3) , Stéphane Trombotto (1)

1 IMP - Ingénierie des Matériaux Polymères
2 LCPO - Laboratoire de Chimie des Polymères Organiques
3 Team 3 LCPO : Polymer Self-Assembly & Life Sciences

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.

Mots clés: chitosan; oligomer; reducing-end; oxyamine; building-block; conjugation

Domaines: Polymères; Matériaux; Matière Molle [cond-mat.soft]

Maxence Coudurier, Jimmy Faivre, Agnès Crépet, Catherine Ladavière, Thierry Delair, et al.. Reducing-End Functionalization of 2,5-Anhydro-d-mannofuranose-Linked Chitooligosaccharides by Dioxyamine: Synthesis and Characterization. Molecules, 2020, 25 (5), pp.1143. ⟨10.3390/molecules25051143⟩. ⟨hal-02530215⟩