title: Aniline-catalyzed reductive amination as a powerful method for the preparation of reducing end-"clickable" chitooligosaccharides.
abstract: Functionalized oligosaccharides are useful intermediates to prepare products for biological research or for the development of advanced functional materials. Here, we report the unprecedented use of aniline as an efficient organocatalyst reaction with "clickable" (azide or alkyne) amine for the transimination-mediated reductive amination of a chitooligosaccharide. Moreover, we demonstrate that alkyne-bearing aniline constitutes an excellent tool for the easy derivatization of chitosan oligosaccharides. Evidence for such improvement has been illustrated by the straightforward design of a FRET substrate to probe chitinase activity and of amphiphilic polycaprolactone-grafted-chitosan. This efficient methodology paves the way to the preparation of novel chitosan oligosaccharide-based advanced materials.
authors: Centre de Recherches sur les Macromolécules Végétales, CERMAV-CNRS (Affiliated with Université Joseph Fourier, member of the Institut de Chimie Moléculaire de Grenoble and of the PolyNat Carnot Institute), BP 53, 38041 Grenoble cedex 9, France.
authors: Alexandre
authors: A
authors: Guerry
authors: Julien
authors: J
authors: Bernard
authors: Eric
authors: E
authors: Samain
authors: Etienne
authors: E
authors: Fleury
authors: Sylvain
authors: S
authors: Cottaz
authors: Sami
authors: S
authors: Halila
mesh_terms: D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002384:Catalysis; D057930:Click Chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D000814:Aniline Compounds; D009844:Oligosaccharides; C023650:aniline