Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase
Author(s)
Bhatt, Beenu
Boehm, Raphael
Kerry, Philip S
Dyason, Jeffrey C
Russell, Rupert JM
Thomson, Robin J
von Itzstein, Mark
Griffith University Author(s)
Year published
2012
Metadata
Show full item recordAbstract
A series of C3 O-functionalized 2-acetamido-2-deoxy-?4-߭D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the in?uenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits in?uenza virus sialidase at a sub-占level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.A series of C3 O-functionalized 2-acetamido-2-deoxy-?4-߭D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the in?uenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits in?uenza virus sialidase at a sub-占level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.
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Journal Title
Journal of Medicinal Chemistry
Volume
55
Issue
20
Copyright Statement
Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
Subject
Medicinal and biomolecular chemistry
Biomolecular modelling and design
Organic chemistry
Organic chemical synthesis
Pharmacology and pharmaceutical sciences