高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (11): 2199.

• 研究论文 • 上一篇    下一篇

透明质酸三糖模拟物的高效合成

魏国华1,2, 杜宇国1, Khushi L. Matta2   

  1. 1. 中国科学院生态环境研究中心环境化学与生态毒理学国家重点实验室, 北京100085;
    2. Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263
  • 收稿日期:2009-03-06 出版日期:2009-11-10 发布日期:2009-11-10
  • 通讯作者: 魏国华, 男, 博士, 副研究员, 主要从事寡糖药物的设计合成研究. E-mail: wgh@rcees.ac.cn
  • 基金资助:

    国家自然科学基金(批准号: 30701043)资助.

Highly Efficient Synthesis of Two Hyaluronan Trisaccharide Analogues for Potential Hyaluronic Acid Synthases Inhibitors

WEI Guo-Hua1,2*, DU Yu-Guo1, Khushi L. Matta2   

  1. 1. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China;
    2. Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA
  • Received:2009-03-06 Online:2009-11-10 Published:2009-11-10
  • Contact: WEI Guo-Hua. E-mail: wgh@rcees.ac.cn
  • Supported by:

    国家自然科学基金(批准号: 30701043)资助.

摘要:

设计合成了2个透明质酸(HA)模拟物12, 通过最小基团MeO的引入修饰, 模拟天然HA片段的特性, 用于透明质酸合成酶(HAS)催化机理与抑制剂的研究.

关键词: 透明质酸; 透明质酸合成酶; 抑制剂; 2-萘基甲基(NAP)

Abstract:

The syntheses of two hyaluronan trisaccharide analogues, naphthyl O-(3-methoxy-β-D-glucopy-ranosyluronic acid)-(1,3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-O-β-D-glucopyranosyluronic acid and naphthyl O-(3-methoxy-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1,4)-O-(β-D-glucopyranosyluronic acid)-(1,3)-O-2-acetamido-2-deoxy-β-D-glucopyranoside, were described. Construction of the target molecules was achieved through a combination of BF3·Et2O/toluene system and trichloroacetimidate glycosylation methodology. This is the first report on the synthesis of the 3-methoxyl derivatives, which represent the smallest fragments that incorporate all the structural features of polymeric hyaluronan and can be used for potential hyaluronic acid synthases inhibitors.

Key words: Hyaluronan; Hyaluronic acid synthase; Inhibitor; 2-Naphthylmethyl(NAP)

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