Exploring the Interactions of Unsaturated Glucuronides with Inﬂuenza Virus Sialidase

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

Issue

DOI

https://doi.org/10.1021/jm301145k

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

Publication URI

http://hdl.handle.net/10072/48670

Collection

Journal articles