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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (24): 2909-2916. 上一篇    下一篇

研究论文

神经节苷脂GM3的有效合成

朱振元1,2, 张勇民*,2,3   

  1. (1天津科技大学食品工程与生物技术学院 天津 300457)
    (2法国巴黎高等师范学院-CNRS-UMR 8642, 24 rue Lhomond, 75231 Paris Cedex 05, France)
    (3浙江大学-巴黎高等师范药物化学联合实验室浙江大学湖滨校区 杭州 310031)
  • 投稿日期:2007-01-10 修回日期:2007-06-20 发布日期:2007-12-28
  • 通讯作者: 张勇民

An Efficient Method for Ganglioside GM3 Preparation

ZHU Zhen-Yuan1,2; ZHANG Yong-Min*,2,3   

  1. (1 College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin 300457)
    (2 Ecole Normale Supérieure, Département de Chimie, CNRS-UMR 8642, 24 rue Lhomond, 75231 Paris Cedex 05, France)
    (3 ZJU-ENS Joint Laboratory of Medicinal Chemistry, Zhejiang University, Hubin Campus, Hangzhou 310031)
  • Received:2007-01-10 Revised:2007-06-20 Published:2007-12-28
  • Contact: ZHANG Yong-Min

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1064

被引次数

6

报道了α-Neu5Ac-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-Cer (GM3)的有效合成方法. 将选择性保护的乳糖二醇与唾液酸黄原酸酯(Xanthate)在AgOTf/PhSCl催化下高立体、高区域选择性糖苷化得到含唾液酸的三糖, 经脱苄基保护及全乙酰化后, 在温和条件下脱去还原端保护基, 并制备成三氯乙酰亚胺酯糖苷, 与选择性保护的鞘氨醇缩合得到含叠氮化合物9. 后者用Ph3P还原后, 在EDC存在下与硬脂酸酰化反应, 得化合物11, 脱去保护基后获得目标产物GM3 (1), 为研究肿瘤疫苗提供有用材料. 化合物结构经NMR, MS和HRMS确证.

关键词: 神经节苷脂, 糖脂, 合成, GM3, 肿瘤疫苗

An efficient synthesis of α-Neu5Ac-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-Cer (GM3) was described. A suitably protected lactoside diol was glycosylated with sialyl xanthate to give only the α-sialyl trisaccharide in good yield based on a highly stereo- and regioselective sialylation. Condensation of the azidosphingosine 8 with the imidate 7 using a promoter TMSOTf, afforded the glycolipid 9, which was directly transformed to 10 by reduction with Ph3P and subsequent acylation with octadecanoic acid in the presence of EDC. After deprotection, the target GM3 was afforded, which can be applied to study of the tumor-vaccine. The structures of these compounds were fully confirmed by 1H and 13C NMR, mass spectra (MS) and HRMS.

Key words: ganglioside, glycolipid, synthesis, GM3, tumor-vaccine