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

doi:10.3390/molecules17089590

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

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

Tomohiro Nohara¹, Akihiro Imamura^1,2,* , Maho Yamaguchi³, Kazuya I. P. J. Hidari³, Takashi Suzuki³, Tatsuya Komori¹, Hiromune Ando^1,2, Hideharu Ishida¹ and Makoto Kiso^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; in revised form: 6 August 2012 / Accepted: 8 August 2012 / Published: 10 August 2012

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)

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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

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MDPI and ACS Style

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.

AMA Style

Nohara T, Imamura A, Yamaguchi M, Hidari KIPJ, 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(8):9590-9620.

Chicago/Turabian Style

Nohara, Tomohiro; Imamura, Akihiro; Yamaguchi, Maho; Hidari, Kazuya I. P. J.; Suzuki, Takashi; Komori, Tatsuya; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto. 2012. "Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses ^†." Molecules 17, no. 8: 9590-9620.

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