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Molecules 2012, 17(8), 9590-9620; doi:10.3390/molecules17089590

Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses

1,2,* , 3
1 Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan 2 Institute for Integrated Cell-Material Sciences, Kyoto University, 69 Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan 3 Department of Biochemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka-shi, Shizuoka 422-8526, Japan Synthetic studies on sialoglycoconjugates, Part 157.
* Authors to whom correspondence should be addressed.
Received: 9 July 2012 / Revised: 6 August 2012 / Accepted: 8 August 2012 / Published: 10 August 2012
(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)
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A novel ganglioside bearing Neua2-3Gal and Neua2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between the non-reducing end of the oligosaccharide and the cyclic glucosylceramide moiety. Examination of its binding activity to influenza A viruses revealed that the new ligand is recognized by Neua2-3 and 2-6 type viruses.
Keywords: ganglioside; sialic acid; total synthesis; glycosylation; influenza virus ganglioside; sialic acid; total synthesis; glycosylation; influenza virus
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Nohara, T.; Imamura, A.; Yamaguchi, M.; Hidari, K.I.P.J.; Suzuki, T.; Komori, T.; Ando, H.; Ishida, H.; Kiso, M. Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses . Molecules 2012, 17, 9590-9620.

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