Abstract
Chitooligosaccharide with one 2,5-anhydro-d-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted octanoic hydrazide-linked COSamf was fully characterized by NMR spectroscopy and MALDI-TOF mass spectrometry. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties.
Highlights
Chitosan is a linear copolymer of β-(1→4)-linked D-glucosamine (GlcN) and N-acetyl (GlcNAc) units in various proportions
We described the original synthesis of octanoic hydrazide–linked chitooligosaccharide-2,5-anhydro-D-mannofuranose
Octanoic hydrazide–linked chitooligosaccharide-2,5-anhydro-D-mannofuranose was efficiently synthesized from chitosan in a two-step procedure involving the reductive amination of chitooligosaccharide-2,5-anhydro-D-mannofuranose (COSamf 1) with octanoic hydrazide as illustrated in Scheme 1
Summary
Chitosan is a linear copolymer of β-(1→4)-linked D-glucosamine (GlcN) and N-acetyl (GlcNAc) units in various proportions. Named chitooligosaccharides (COS), have recently received considerable attention as functional biomolecules with a wide range of potential applications in food, agriculture, medicine, pharmaceutics and cosmetics [5,6]. The interest of this work is to take advantage of the reactivity of the “non-masked” aldehyde group of the 2,5-anhydro-D-mannofuranose (amf) unit present at the reducing end of COS produced by the nitrous acid depolymerization of chitosan. It should open opportunities for preparing numerous COS-based functional materials with amphiphilic properties
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