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一种抗转移层粘连蛋白核心三糖的合成

金晓锋, 孟祥豹, 廖凯俊, 李庆, 李中军*   

  1. 北京大学 天然药物及仿生药物国家重点实验室; 药学院 化学生物学系, 北京100191
  • 收稿日期:2008-05-25 修回日期:2008-11-10 出版日期:2008-12-15 发布日期:2008-12-15
  • 通讯作者: 李中军*

Facile synthesis of a core trisaccharide of laminin as a potential metastatic antagonist

Xiao-Feng Jin, Xiang-Bao Meng, Kai-Jun Liao, Qing Li, Zhong-Jun Li*
  

  1. The State Key Laboratory of Natural and Biomimetic Drugs;
    Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
  • Received:2008-05-25 Revised:2008-11-10 Online:2008-12-15 Published:2008-12-15
  • Contact: Zhong-Jun Li*

摘要:

本文完成了一种具有潜在转移活性的层粘连蛋白核心三糖β-D-Gal-(1→4)-β-D-GlcpNAc-(1→6)-α-D-Manp-OMe的合成。以2-碘代叠氮乳糖为供体采用叠氮碘糖基化反应一步完成了2-脱氧-2-氨基乳糖结构及1,2-反式-氨基乳糖糖苷键的立体选择性构建。这种方法能简易、高效地合成含氨基乳糖的寡糖, 较好地避免了直接使用活性较差的2-氨基糖衍生物构建氨基乳糖模块。

关键词: 叠氮碘糖基化, 叠氮碘糖基化, 叠氮碘糖基化, 乳糖烯, 乳糖烯, 乳糖烯, 2-碘代叠氮糖, 2-碘代叠氮糖, 2-碘代叠氮糖, 氨基乳糖苷, 氨基乳糖苷, 氨基乳糖苷

Abstract:

A core trisaccharide of laminin, β-D-Gal-(14)-β-D-GlcpNAc-(16)-α-D-Manp-OMe, with potential anti-tumor metastatic activity was designed and prepared. 2-Iodoglactosyl azide was used as the donor to construct 2-N-acetamido-2-deoxylactosyl moiety through an azidoiodo-glycosylation reaction. Simultaneously, 1, 2-trans-β-glycosic bond was formed stereoselectively in one step with a moderate yield. This novel procedure avoided the use of 2-amino-2-deoxyglucose as both donor and acceptor.

Key words: Azidoiodo-glycosylation, Azidoiodo-glycosylation, Lactal, Lactal, 2-Iodoglycosyl azide, 2-Iodoglycosyl azide, Lactosamine, Lactosamine, ,

Supporting: Foundation items: National Science Foundation of China (Grant No. 20732001 and 90713004).
*Corresponding author. Tel.: 86-10-82801714