Chemical Synthesis of N-Acetylchitooligosaccharide Analogues

Chem. J. Chinese Universities

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Chemical Synthesis of N-Acetylchitooligosaccharide Analogues

YAO Yan-Ping^1,2, ZHU Zhen-Yuan², XU Tong¹, ZHANG Yong-Min^2,3

1. Department of Plant Protection, College of Agriculture Biotechnology, Zhejiang University, Hangzhou 310029, China;
2. Ecole Normale Supérieure, Département de Chimie, Associéau CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France;
3. ZJU-ENS Joint Laboratory of Medicinal Chemistry, Zhejiang University, Hangzhou 310031, China

Received:2006-02-28 Revised:1900-01-01 Online:2007-02-10 Published:2007-02-10
Contact: ZHANG Yong-Min

Abstract

Abstract: It has been reported that N-acetylchitooligosaccharides can act as the chemical signals in the plant induced resistance. In order to study the mechanisms and search new compounds with a high biological activity, utilizing N-phthalic acyle group as the protective group of amine, and thioethyl as the leaving group at the reducing terminal, two novel N-acetylchitooligosaccharide analogues, β-1,3-N-acetamido-gluco-disaccharide and β-1,3-N-acetamido-gluco-trisaccharide, were designed and synthesized by amino glucose as the starting material. All synthesized compounds were characterized by ¹H NMR, ¹³C NMR and HRMS. Being different with the natural N-acetylchitooligosaccharides, the two synthesized analogues have a backbone of 1→3 linked structure, and they can be applied to study of the relationship between the induced resistance of plants to diseases by N-acetylchitooligosaccharides and the backbone structures.

Key words: N-Acetylchitooligosaccharide analogues, β-1,3-N-Acetamido-gluco-disaccharide, β-1,3-N-Acetamido-gluco-trisaccharide

CLC Number:

O629.12
Q625

TrendMD:

YAO Yan-Ping^1,2, ZHU Zhen-Yuan², XU Tong¹, ZHANG Yong-Min^2,3. Chemical Synthesis of N-Acetylchitooligosaccharide Analogues[J]. Chem. J. Chinese Universities, doi: .

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Chemical Synthesis of N-Acetylchitooligosaccharide Analogues

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