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Issue 12, 2009
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Galactose-conjugates of the oseltamivir pharmacophore—new tools for the characterization of influenza virus neuraminidases

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Abstract

We describe the synthesis of mimetics of the α2–3 and α2–6 sialogalactoside substrates of influenza neuraminidase which include the oseltamivir pharmacophore, and report the sub-nanomolar affinities for these novel neuraminidase inhibitors. The challenge of synthesizing a Phospha-Oseltamivir/Tamiphosphor monoester involving the secondary 3-hydroxy group of galactose required to mimic the α2–3 sialogalactoside has been overcome by palladium-promoted coupling of the oseltamivir-derived vinyl iodide with a protected galactose-3-phosphonate. The difference in binding of these two inhibitors to a given influenza neuraminidase should be a function of its α2–3/α2–6-selectivity, an important, but not yet fully understood factor in the adaptation of highly pathogenic avian influenza viruses to human hosts.

Graphical abstract: Galactose-conjugates of the oseltamivir pharmacophore—new tools for the characterization of influenza virus neuraminidases

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Publication details

The article was received on 17 Feb 2009, accepted on 20 Mar 2009 and first published on 23 Apr 2009


Article type: Paper
DOI: 10.1039/B903394G
Citation: Org. Biomol. Chem., 2009,7, 2570-2575
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    Galactose-conjugates of the oseltamivir pharmacophore—new tools for the characterization of influenza virus neuraminidases

    B. Carbain, S. R. Martin, P. J. Collins, P. B. Hitchcock and H. Streicher, Org. Biomol. Chem., 2009, 7, 2570
    DOI: 10.1039/B903394G

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