4-(Hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose

Emil Salim , Alice Galais (1) , Stéphane Trombotto (1)

1 IMP - Ingénierie des Matériaux Polymères

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.

Mots clés: chitosan; chitooligosaccharide-2; 5-anhydro-D-mannofuranose; 4-(hexyloxy)aniline; nitrous deamination; reductive amination

Domaines: Polymères; Matériaux

Emil Salim, Alice Galais, Stéphane Trombotto. 4-(Hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose. Molbank, 2014, 14, pp.1. ⟨10.3390/M815⟩. ⟨hal-00988237⟩