Degradation of Target Oligosaccharides by Anthraquinone–Lectin Hybrids with Light Switching

Authors

  • Yukari Imai,

    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan), Fax: (+81) 45-566-1576
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  • Shingo Hirono,

    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan), Fax: (+81) 45-566-1576
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  • Haruka Matsuba,

    1. Department of Applied Biological Chemistry, Faculty of Agriculture, and/or Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Shizuoka 422-8529 (Japan)
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  • Dr. Tomohiro Suzuki,

    1. Department of Applied Biological Chemistry, Faculty of Agriculture, and/or Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Shizuoka 422-8529 (Japan)
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  • Dr. Yuka Kobayashi,

    1. Department of Applied Biological Chemistry, Faculty of Agriculture, and/or Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Shizuoka 422-8529 (Japan)
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  • Prof. Dr. Hirokazu Kawagishi,

    1. Department of Applied Biological Chemistry, Faculty of Agriculture, and/or Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Shizuoka 422-8529 (Japan)
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  • Dr. Daisuke Takahashi,

    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan), Fax: (+81) 45-566-1576
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  • Prof. Dr. Kazunobu Toshima

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan), Fax: (+81) 45-566-1576
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan), Fax: (+81) 45-566-1576

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Abstract

Anthraquinone–lectin hybrids were effectively synthesized using water-soluble anthraquinone derivative with concanavalin A (ConA) and hygrophorus russula lectin (HRL) to give anthraquinone–ConA () and anthraquinone–HRL (17) hybrids, respectively. These anthraquinone–lectin hybrids effectively and selectively degraded oligosaccharides containing a mannose residue as a non-reducing terminal sugar, which has affinity for ConA and HRL, under photo-irradiation with long-wavelength UV light without additives and under neutral conditions. In addition, anthraquinone–HRL (17) selectively photo-degraded only Man(α1,6)Man, which has a high affinity for HRL, among several mannosides by recognition of both the type and glycosidic linkage profile of the sugar in an oligosaccharide.

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