A sialosyl sulfonate as a potent inhibitor of influenza virus replication
Author(s)
Hadhazi, Adam
Pascolutti, Mauro
Bailly, Benjamin
Dyason, Jeffrey C
Borbas, Aniko
Thomson, Robin J
von Itzstein, Mark
Year published
2017
Metadata
Show full item recordAbstract
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.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.
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Journal Title
Organic and Biomolecular Chemistry
Volume
15
Issue
25
Subject
Bioinorganic chemistry
Medicinal and biomolecular chemistry
Organic chemistry