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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*

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, ,

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