1,5-Lactamized Sialyl Acceptors for Various Disialoside Syntheses: Novel Method for the Synthesis of Glycan Portions of Hp-s6 and HLG-2 Gangliosides

Authors

  • Hiromune Ando Dr.,

    1. Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan, Fax: (+81) 58-293-2617
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  • Yusuke Koike,

    1. Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan, Fax: (+81) 58-293-2918
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  • Sachiko Koizumi,

    1. Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan, Fax: (+81) 58-293-2918
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  • Hideharu Ishida Dr.,

    1. Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan, Fax: (+81) 58-293-2918
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  • Makoto Kiso Dr.

    1. Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan, Fax: (+81) 58-293-2918
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  • Synthetic Studies on Sialoglycoconjugates, Part 139. This work was financially supported by CREST of JST (M.K.), MEXT of Japan (Grant-in-Aid for Scientific Research; no. 16780083 to H.A., no. 16580086 to H.I., and no. 17101007 to M.K.), and the Mitsubishi Chemical Corporation Fund (H.A.). We thank Ms. Kiyoko Ito for technical assistance. For Part 138, see: M. Yamaguchi, H. Ishida, A. Kanamori, R. Kannagi, M. Kiso, Glycoconjugate J.2005, 22, 83–96.

Abstract

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Drastisch gesteigert wird die Reaktivität der C4- und C8-Hydroxygruppen der Sialinsäure durch die Bildung einer 1,5-Lactambrücke. Dies machte Sialyl-α(2→4)sialosid und Sialyl-α(2→8)sialosid in hohen Ausbeuten durch direkte Sialylierung zugänglich (siehe Schema). Des Weiteren gelang die erste Synthese der Glycanteile der neuen Ganglioside Hp-s6 und HLG-2.

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