Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality
Identifieur interne : 000E05 ( Ncbi/Curation ); précédent : 000E04; suivant : 000E06Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality
Auteurs : Christopher J. Vavricka [Japon] ; Chiaki Muto [Japon] ; Tomohisa Hasunuma [Japon] ; Yoshinobu Kimura [Japon] ; Michihiro Araki [Japon] ; Yan Wu [République populaire de Chine] ; George F. Gao [République populaire de Chine] ; Hiroshi Ohrui [Japon] ; Minoru Izumi [Japon] ; Hiromasa Kiyota [Japon]Source :
- Scientific Reports [ 2045-2322 ] ; 2017.
Abstract
The design, synthesis and application of
Url:
DOI: 10.1038/s41598-017-07836-y
PubMed: 28811524
PubMed Central: 5557986
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PMC:5557986Le document en format XML
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<author><name sortKey="Vavricka, Christopher J" sort="Vavricka, Christopher J" uniqKey="Vavricka C" first="Christopher J." last="Vavricka">Christopher J. Vavricka</name>
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<front><div type="abstract" xml:lang="en"><p id="Par1">The design, synthesis and application of <italic>N</italic>
-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>
-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>
-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-<italic>N</italic>
-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.</p>
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