Synthesis and characterization of nucleophilic polysaccharide carbazates

Katja Geitel; Hendryk Würfel; Wolfgang Günther; Thomas Heinze

doi:10.1016/j.carbpol.2023.121727

Synthesis and characterization of nucleophilic polysaccharide carbazates

Carbohydr Polym. 2024 Apr 1:329:121727. doi: 10.1016/j.carbpol.2023.121727. Epub 2023 Dec 24.

Authors

Katja Geitel¹, Hendryk Würfel¹, Wolfgang Günther¹, Thomas Heinze²

Affiliations

¹ Friedrich Schiller University Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Center of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany.
² Friedrich Schiller University Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Center of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, Germany. Electronic address: Thomas.heinze@uni-jena.de.

PMID: 38286527
DOI: 10.1016/j.carbpol.2023.121727

Abstract

A simple synthesis of amino polysaccharides (PS) could be developed. Phenyl carbonates (PC) of xylan, dextran, and cellulose were easily transferred into PS carbazates by conversion with hydrazine hydrate. The degree of substitution could be adjusted by varying the molar ratio of hydrazine to PS repeating unit, enabling the preparation of both pure PS carbazates and derivatives with bifunctional reactivity containing the reactive PC and the amino group of the carbazate moiety. Further functionalization of the derivatives is feasible with carbonyl compounds like aldehydes at the carbazate groups. The reactivity of carbazate groups is shown by the reaction with 4-fluorobenzaldehyde, resulting in the formation of Schiff base conjugates.

Keywords: Hydrazine hydrate; Polysaccharide carbazates; Polysaccharide phenyl carbonates.