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Molbank 2014, 2014(1), M815; doi:10.3390/M815

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

Ingénierie des Matériaux Polymères (IMP, UMR CNRS 5223), Université Claude Bernard Lyon 1, Université de Lyon, Villeurbanne F-69622, France
Department of Chemistry, Institut Teknologi Bandung, Bandung 40132, Indonesia
Author to whom correspondence should be addressed.
Received: 17 January 2014 / Accepted: 8 February 2014 / Published: 12 February 2014
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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.
Keywords: chitosan; chitooligosaccharide-2,5-anhydro-D-mannofuranose; 4-(hexyloxy)aniline; nitrous deamination; reductive amination chitosan; chitooligosaccharide-2,5-anhydro-D-mannofuranose; 4-(hexyloxy)aniline; nitrous deamination; reductive amination

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Salim, E.; Galais, A.; Trombotto, S. 4-(Hexyloxy)aniline-linked chitooligosaccharide-2,5-anhydro-D-mannofuranose. Molbank 2014, 2014, M815.

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