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Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality.
Vavricka, Christopher J; Muto, Chiaki; Hasunuma, Tomohisa; Kimura, Yoshinobu; Araki, Michihiro; Wu, Yan; Gao, George F; Ohrui, Hiroshi; Izumi, Minoru; Kiyota, Hiromasa.
Afiliación
  • Vavricka CJ; Graduate School of Environmental and Life Science, Okayama University, Okayama, 700-8530, Japan. chrisv@people.kobe-u.ac.jp.
  • Muto C; Graduate School of Science, Technology and Innovation, Kobe University, Kobe, 657-0013, Japan. chrisv@people.kobe-u.ac.jp.
  • Hasunuma T; Graduate School of Environmental and Life Science, Okayama University, Okayama, 700-8530, Japan.
  • Kimura Y; Graduate School of Science, Technology and Innovation, Kobe University, Kobe, 657-0013, Japan.
  • Araki M; Graduate School of Environmental and Life Science, Okayama University, Okayama, 700-8530, Japan.
  • Wu Y; Graduate School of Science, Technology and Innovation, Kobe University, Kobe, 657-0013, Japan.
  • Gao GF; CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China.
  • Ohrui H; CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China.
  • Izumi M; Yokohama College of Pharmacy, Yokohama, 245-0066, Japan.
  • Kiyota H; Graduate School of Environmental and Life Science, Okayama University, Okayama, 700-8530, Japan.
Sci Rep ; 7(1): 8239, 2017 08 15.
Article en En | MEDLINE | ID: mdl-28811524
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Siálicos / Inhibidores Enzimáticos Idioma: En Revista: Sci Rep Año: 2017 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido
Texto completo
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PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ácidos Siálicos / Inhibidores Enzimáticos Idioma: En Revista: Sci Rep Año: 2017 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido