Aniline-Catalyzed Reductive Amination as a Powerful Method for the Preparation of Reducing End-鈥淐lickable鈥?Chitooligosaccharides

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• 作者：Alexandre Guerry ; Julien Bernard ; Eric Samain ; Etienne Fleury ; Sylvain Cottaz ; Sami Halila
• 刊名：Bioconjugate Chemistry
• 出版年：2013
• 出版时间：April 17, 2013
• 年：2013
• 卷：24
• 期：4
• 页码：544-549
• 全文大小：285K
• 年卷期：v.24,no.4(April 17, 2013)
• ISSN：1520-4812

文摘

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 鈥渃lickable鈥?(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.