Abstract
Chitooligosaccharide with one 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan. The oxidation of the amf-unit by chlorite sodium was achieved in high yield. The chemical structure of the targeted chitooligosaccharide-2,5-anhydro-D-mannonic acid with a degree of polymerization ~10 was fully characterized by NMR spectroscopy, MALDI-TOF mass spectrometry and size-exclusion chromatography. The success of this synthesis opens the way to a new generation of end-functionalized COS building blocks.
Highlights
Chitooligosaccharide with one 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan
We describe here the synthesis and the characterisation of chitooligosaccharide-2,5-anhydro-D-mannonic acid with a low degree of polymerization (DP) ~10 by reaction of COSamf with sodium chlorite
The chemical structure of COSamf 1 was fully confirmed by 1H and 13C-NMR spectroscopies, MALDI-TOF mass spectrometry and size-exclusion chromatography
Summary
Chitooligosaccharide with one 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan. We describe here the synthesis and the characterisation of chitooligosaccharide-2,5-anhydro-D-mannonic acid with a low degree of polymerization (DP) ~10 by reaction of COSamf with sodium chlorite. Chitooligosaccharide-2,5-anhydro-D-mannonic acid with an average GlcN-units number into chains around 10, was efficiently synthesized from chitosan in a one pot two-step procedure involving the aldehyde group oxidation of the intermediate chitooligosaccharide-2,5-anhydro-D-mannofuranose (COSamf 1) with sodium chlorite as illustrated in Scheme 1.
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