Synthesis of pyridine-free xylan sulfates

Annett Pfeifer; Thomas Heinze

doi:10.1016/j.carbpol.2018.10.119

Synthesis of pyridine-free xylan sulfates

Carbohydr Polym. 2019 Feb 15:206:65-69. doi: 10.1016/j.carbpol.2018.10.119. Epub 2018 Nov 2.

Authors

Annett Pfeifer¹, Thomas Heinze²

Affiliations

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

PMID: 30553369
DOI: 10.1016/j.carbpol.2018.10.119

Abstract

The usual sulfation of polysaccharides applying chlorosulfuric acid and pyridine may form products containing pyridine-based impurities, which may yield toxic side effects. The synthesis of pyridine-free polysaccharide sulfates could be realized simply by using xylan that was treated with a reducing agent (NaBH₄) prior to the sulfation reaction. The reduced xylan possess same reactivity compared to untreated xylan. The purity of the alternatively synthesized xylan sulfate is proofed by NMR spectroscopic studies. Thus, the simple reduction of the reducing end groups of the polysaccharide prior the sulfation is an efficient tool to get pure products, which may be scaled up easily.

Keywords: NMR spectroscopy; Polysaccharides; Pyridine; Sulfation, xylan sulfate; Xylan.