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一种抗转移层粘连蛋白核心三糖的合成
引用本文:金晓锋,孟祥豹,廖凯俊,李庆,李中军.一种抗转移层粘连蛋白核心三糖的合成[J].中国药学,2008,17(4):272-276.
作者姓名:金晓锋  孟祥豹  廖凯俊  李庆  李中军
作者单位: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
基金项目:Foundation items: National Science Foundation of China (Grant No 20732001 and 90713004). Acknowledgements We gratefully acknowledge the support of this study by a grant from National Science Foundation of China (Grant No. 20732001 and 90713004).
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  乳糖烯  2-碘代叠氮糖  氨基乳糖苷

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 The State Key Laboratory of Natural and Biomimetic Drugs.Facile synthesis of a core trisaccharide of laminin as a potential metastatic antagonist[J].Journal of Chinese Pharmaceutical Sciences,2008,17(4):272-276.
Authors:Xiao-Feng Jin Xiang-Bao Meng Kai-Jun Liao Qing Li Zhong-Jun Li The State Key Laboratory of Natural and Biomimetic Drugs
Institution:Xiao-Feng Jin Xiang-Bao Meng Kai-Jun Liao Qing Li Zhong-Jun Li The State Key Laboratory of Natural and Biomimetic Drugs,Department of Chemical Biology,School of Pharmaceutical Sciences,Peking University,Beijing 100191,China
Abstract:A core trisaccharide of laminin, β-D-Gal-(1→4)-β-D-GlcpNAc-(1→6)-α-D-Manp-OMe, with potential anti-rumor 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.
Keywords:Azidoiodo-glycosylation  Lactal  2-Iodoglycosyl azide  Lactosamine
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