Carbain, Benoit, Martin, Stephen R, Collins, Patrick J, Hitchcock, Peter B and Streicher, Hansjorg (2009) Galactose-conjugates of the oseltamivir pharmacophore-new tools for the characterization of influenza virus neuraminidases. Organic and Biomolecular Chemistry, 7 (12). pp. 2570-2575. ISSN 1477-0520

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Abstract

We describe the synthesis of mimetics of the a23 and a26 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 a23 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 a23/a26-selectivity, an important, but not yet fully understood factor in the adaptation of highly pathogenic avian influenza viruses to human hosts.

Item Type:	Article
Schools and Departments:	School of Life Sciences > Chemistry
Depositing User:	Benoit Carbain
Date Deposited:	06 Feb 2012 18:11
Last Modified:	14 May 2012 15:41
URI:	http://sro.sussex.ac.uk/id/eprint/15119

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