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A First Total Synthesis of a Hybrid-Type Ganglioside Associated with Amyotrophic Lateral Sclerosis-Like Disorder

Authors

  • Shinya Nakashima,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Dr. Hiromune Ando,

    Corresponding author
    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
    • Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Dr. Akihiro Imamura,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Dr. Nobuhiro Yuki,

    1. Departments of Microbiology & Medicine, National University of Singapore, 5 Science Drive 2, Blk MD4A, Level 5, Singapore 117597
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  • Dr. Hideharu Ishida,

    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Dr. Makoto Kiso

    Corresponding author
    1. Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
    2. Department of Applied Bioorganic Chemistry, Institute for Integrated Cell-Material Sciences (WPI program), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501 (Japan)
    • Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193 (Japan), Fax: (+81) 58-293-3452
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  • Synthetic studies on sialoglycoconjugates, Part 151; for Part 150, see: T. Komori, A. Imamura, H. Ando, H. Ishida, M. Kiso, Carbohydr. Res.2009, 344, 1453–1463.

Abstract

The hybrid ganglioside X1, which was identified in the bovine brain, was synthesized for the first time. Ganglioside X1 is believed to be involved in the development of amyotrophic lateral sclerosis-like disorders in patients with neurological disorders after treatment with bovine brain gangliosides. A convergent approach using two branched glycan units, the GM2-core trisaccharide and the lacto-ganglio tetrasaccharide, efficiently provided the highly branched heptasaccharide part of ganglioside X1, which was conjugated with the ceramide part to produce the protected ganglioside X1. Global deprotection delivered homogenous ganglioside X1, with which serum from the patient was reacted.

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