DNA–Carbohydrate Recognition: Design and Synthesis of an Eight-Base Sequence-Selective DNA-Binding Oligosaccharide

Authors

  • Prof. K. C. Nicolaou,

    Corresponding author
    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
    • Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Keiichi Ajito,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Hironori Komatsu,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Brian M. Smith,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Dr. Tianhu Li,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Miles G. Egan,

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • Dr. Luigi Gomez-Paloma

    1. Department of Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA) and Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA). Telefax: Int. code +(619) 554-6738
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  • This work was finacially supported by the National Institutes of Health (USA) and the University of California (Biotechnology Grant). Fellowship from Meiji Seika Kaisha, Ltd. (visiting scientist, K. A.), Mitsui Toatsu Chemicals, Inc. (visiting scientist, H. K.), and the Universitá Degli Studi Di Napoli “Frederico II” (visiting assistant professor, L. G. P.) are gratefully acknowledged.

Abstract

A decacyclic oligosaccharide was designed to dock into the minor groove of duplex DNA selectively at a TCCTXXAGGA sequence. Competition experiments with calicheamicin γmath image revealed that the oligosaccharide inhibits DNA cleavage and exhibits high DNA binding affinity.

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