Abstract
Low molecular weight 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 functionalization of the amf unit by reductive amination with 4-(hexyloxy)aniline in presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted 4-(hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose was fully characterized by NMR spectroscopy, MALDI-TOF mass spectrometry and size-exclusion chromatography. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties.
Highlights
Low molecular weight chitooligosaccharide with one 2,5-anhydro-Dmannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan
We described the synthesis of the 4-(hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose
The interest of this work is to take advantage of the reactivity of the aldehyde group of the 2,5-anhydro-D-mannofuranose unit present at the reducing end of COS obtained by nitrous deamination of chitosan, to generate original amphiphilic
Summary
Low molecular weight chitooligosaccharide with one 2,5-anhydro-Dmannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan. We described the synthesis of the 4-(hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose. Synthesis of the 4-(hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydroD-mannofuranose from chitosan.
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