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A sialosyl sulfonate as a potent inhibitor of influenza virus replication†
Mauro Pascolutti,Benjamin Bailly,Jeffrey C. Dyason,Anikó Borbás,Robin J. Thomson,Mark von Itzstein
Organic & Biomolecular Chemistry Pub Date : 05/17/2017 00:00:00 , DOI:10.1039/C7OB00947J
Abstract

A new direction for influenza virus sialidase inhibitor development was identified using a sulfonate congener of 2-deoxy-2-β-H N-acetylneuraminic acid. Sialosyl sulfonates can be synthesised efficiently in four steps from N-acetylneuraminic acid via a microwave assisted decarboxylation. The presence of the sulfonate group significantly increases inhibition of influenza virus sialidase and viral infection when compared to the carboxylate congener, and also to the benchmark sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid, Neu5Ac2en.

Graphical abstract: A sialosyl sulfonate as a potent inhibitor of influenza virus replication
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