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

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

1
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1,2,* , 3
,
3
,
3
,
1
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1,2
,
1
 and
1,2,*
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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Abstract

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 3.0).

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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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