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Paper

Org. Biomol. Chem., 2010, 8, 128 - 136, DOI: 10.1039/b914193f

Total synthesis of LeA-LacNAc pentasaccharide as a ligand for Clostridium difficile toxin A

Ping Zhang, Kenneth Ng and Chang-Chun Ling

The toxins TcdA and TcdB produced by the human pathogen Clostridium difficile gain entrance to host epithelial cells by recognizing cell-surface carbohydrate ligands. Inhibiting the attachment of these toxins to host cells has been proposed to be a viable therapy to treat C. difficile infections. Glycan array screening previously revealed that the LeA-LacNAc pentasaccharide binds strongly to TcdA. Here we report the efficient syntheses of the pentasaccharide and a structurally related tetrasaccharide motif. These compounds will be used to better define the carbohydrate-binding specificity of toxins from C. difficile, which will hopefully lead to the development of improved therapeutics.

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