FullText URL Sci_Rep_15_7_8239.pdf
Author Vavrick, Christopher J.| Muto, Chiaki| Hasunuma, Tomohisa| Kimura, Yoshinobu| Araki, Michihiro| Wu, Yan| Gao, George F.| Ohrui, Hiroshi| Izumi, Minoru| Kiyota, Hiromasa|
Abstract 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.
Note This is an article published by Science
Published Date 2017-08
Publication Title Scientific Reports
Volume volume7
Issue issue1
Publisher Nature Publishing Group
Start Page 8239
ISSN 2045-2322
Content Type Journal Article
language 英語
OAI-PMH Set 岡山大学
Copyright Holders https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
File Version publisher
PubMed ID 28811524
DOI 10.1038/s41598-017-07836-y
Web of Sience KeyUT 000407570000116
Related Url https://doi.org/10.1038/s41598-017-07836-y
FullText URL 17P-SO3-Sia-SR.pdf
Author Vavricka, Christopher J.| Muto, Chiaki| Hasunuma, Tomohisa| Kimura, Yoshinobu| Araki, Michihiro| Wu, Yan| Gao, George F.| Ohrui, Hiroshi| Izumi, Minoru| Kiyota, Hiromasa|
Abstract 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.
Keywords Antiviral agents Drug discovery and development Glycosides
Published Date 2017-08
Publication Title Scientific Reports
Volume volume7
Issue issue1
Publisher Nature Publishing Group
Start Page 8239
ISSN 2045-2322
Content Type Journal Article
language 英語
OAI-PMH Set 岡山大学
Copyright Holders https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
File Version publisher
PubMed ID 28811524
DOI 10.1038/s41598-017-07836-y
Web of Sience KeyUT 000407570000116
Related Url https://doi.org/10.1038/s41598-017-07836-y