ID 55344
フルテキストURL
著者
Vavricka, Christopher J. Graduate School of Environmental and Life Science, Okayama University
Muto, Chiaki Graduate School of Environmental and Life Science, Okayama University
Hasunuma, Tomohisa Graduate School of Science, Technology and Innovation, Kobe University
Kimura, Yoshinobu Graduate School of Environmental and Life Science, Okayama University
Araki, Michihiro Graduate School of Science, Technology and Innovation, Kobe University
Wu, Yan CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences
Gao, George F. CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences
Ohrui, Hiroshi Yokohama College of Pharmacy
Izumi, Minoru Graduate School of Environmental and Life Science, Okayama University
Kiyota, Hiromasa Graduate School of Environmental and Life Science, Okayama University
抄録
The design, synthesis and application of N-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-N-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-N-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-N-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.
キーワード
Antiviral agents
Drug discovery and development
Glycosides
発行日
2017-08
出版物タイトル
Scientific Reports
7巻
1号
出版者
Nature Publishing Group
開始ページ
8239
ISSN
2045-2322
資料タイプ
学術雑誌論文
言語
English
OAI-PMH Set
岡山大学
著作権者
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
論文のバージョン
publisher
PubMed ID
DOI
Web of Sience KeyUT
関連URL
https://doi.org/10.1038/s41598-017-07836-y
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