First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids
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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.
KeywordsCarbohydrate Interaction Lewisx Glycosphingolipid Synthesis
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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