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

Ping Zhang; Kenneth Ng; Chang-Chun Ling

doi:10.1039/B914193F

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Organic & Biomolecular Chemistry

Issue 1, 2010

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

Ping Zhang , Kenneth Ng and Chang-Chun Ling

Org. Biomol. Chem., 2010, 8, 128-136

DOI: 10.1039/B914193F
Received 15 Jul 2009, Accepted 02 Oct 2009
First published on the web 13 Nov 2009

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Abstract
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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 Le^A-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.

Supplementary Info

Additional experimental procedures for compounds 12, 14–15, 17–18, 25–26, 28–30 and ¹H and ¹³C NMR spectra of all synthesized compounds
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Organic & Biomolecular Chemistry

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

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