高等学校化学学报

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几丁寡糖结构类似物的化学合成

姚艳平1,2, 朱振元2, 徐同1, 张勇民2,3   

    1. 浙江大学农业与生物技术学院植物保护系, 杭州 310029;
    2. Ecole Normale Supérieure, Département de Chimie, Associé au CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France;
    3. 浙江大学-巴黎高师药物化学联合实验室, 浙江大学, 杭州 310031
  • 收稿日期:2006-02-28 修回日期:1900-01-01 出版日期:2007-02-10 发布日期:2007-02-10
  • 通讯作者: 张勇民

Chemical Synthesis of N-Acetylchitooligosaccharide Analogues

YAO Yan-Ping1,2, ZHU Zhen-Yuan2, XU Tong1, ZHANG Yong-Min2,3   

    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

摘要: 合成了两个结构新颖的几丁寡糖结构类似物: β-1,3连接的乙酰氨基葡聚二糖和β-1,3连接的乙酰氨基葡聚三糖, 并通过核磁共振和质谱分析确证了其化学结构. 与天然的几丁寡糖不同, 本文所合成的葡聚二糖和葡聚三糖均采取了1→3糖苷键的连接方式, 为研究几丁寡糖诱导植物抗病活性与寡糖区域异构体之间的关系提供有用材料.

关键词: 几丁寡糖类似物, β-1,3-N-乙酰氨基葡聚二糖, β-1,3-N-乙酰氨基葡聚三糖

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

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