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First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids

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Abstract

The Lewisx–Lewisx interaction has been increasingly studied, using a variety of techniques including nuclear magnetic resonance spectroscopy, mass spectrometry, vesicle adhesion, atomic force microscopy, and surface plasmon resonance spectroscopy. However, the detailed molecular mechanism of these weak, divalent cation dependent interactions remains unclear, and new models are needed to probe the nature of this phenomenon in term of key roles of the different hydroxyl groups on Lewisx trisaccharide determinant involved in the Lewisx–Lewisx interaction. An interesting solution is to synthesize a series of Lewisx pentaosyl glycosphingolipid derivatives in which one of the eight hydroxyl groups of Lewisx trisaccharide is replaced by a hydrogen atom, and to test the adhesion induced by interaction of these derivatives, in order to gain insight into the functions played by the hydroxyl groups of the Lewisx trisaccharide. This article describes the synthesis of 3d-deoxy and 4d-deoxy Lewisx pentaosyl glycosphingolipids, to be used for study of the Lewisx–Lewisx interaction.

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Acknowledgements

We thank Dr. Stephen Anderson for assistance in editing of the manuscript. This work is dedicated to Professor Pierre Sinaÿ. We thank the French Embassy in China for a Ph.D fellowship to Y. Luo, the China Scholarship Council and Guizhou University for a Ph.D fellowship to D. Dong. Financial supports from the Centre National de la Recherche Scientifique (CNRS), the Ecole Normale Supérieure (ENS) and the Zhejiang University (ZJU) are gratefully acknowledged.

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Authors and Affiliations

  1. ZJU–ENS joint laboratory of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China

    Yun Luo, Yongzhou Hu & Yongmin Zhang

  2. Département de Chimie, UMR 8642: CNRS–ENS–UPMC, Ecole Normale Supérieure, 24 rue Lhomond, 75231, Paris Cedex 05, France

    Yun Luo, Dengxiang Dong & Yongmin Zhang

  3. Institut de Chimie Moléculaire (FR 2769), Université Pierre et Marie Curie—Paris 6, 75005, Paris, France

    Yun Luo, Dengxiang Dong & Yongmin Zhang

  4. Interfaces, Traitements, Organisation et Dynamique des Systèmes (ITODYS) CNRS–UMR 7086, Université Paris 7—Denis Diderot, 1 rue Guy de la Brosse, 75005, Paris, France

    Chafika Gourmala, Florent Barbault & Botao Fan

  5. Guiyang College of Traditional Chinese Medicine, Guiyang, People’s Republic of China

    Dengxiang Dong

Authors
  1. Yun Luo
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  2. Chafika Gourmala
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  3. Dengxiang Dong
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  4. Florent Barbault
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  6. Yongzhou Hu
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  7. Yongmin Zhang
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Corresponding author

Correspondence to Yongmin Zhang.

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Botao Fan: Deceased October 22, 2006

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Luo, Y., Gourmala, C., Dong, D. et al. First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids. Glycoconj J 25, 335–344 (2008). https://doi.org/10.1007/s10719-007-9077-5

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  • DOI: https://doi.org/10.1007/s10719-007-9077-5

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