An Antibody-Catalyzed 1,2-Rearrangement of Carbon[BOND]Carbon Bonds

Authors

  • Dr. Yuanwei Chen,

    1. Departments of Molecular Biology and Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA), Telefax: Int. code + (619)554-9899
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  • Prof. Jean-Louis Reymond,

    Corresponding author
    1. Departments of Molecular Biology and Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA), Telefax: Int. code + (619)554-9899
    • Departments of Molecular Biology and Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA), Telefax: Int. code + (619)554-9899
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  • Prof. Richard A. Lerner

    Corresponding author
    1. Departments of Molecular Biology and Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA), Telefax: Int. code + (619)554-9899
    • Departments of Molecular Biology and Chemistry, The Scripps Research Institute, 10666 North Torrey Pines Road, La Jolla, CA 92037 (USA), Telefax: Int. code + (619)554-9899
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  • We thank the National Institutes of Health (GM 49736 to J.-L. R.) for financial support.

Abstract

original image

The transition state of the dienone-phenol rearrangement of 1 to 2 is mimicked by hapten 3. An immune response to 3 yielded an antibody (62C7) which was found to catalyze the rearrangement efficiently. It was shown that 62C7 does not act as a simple acid catalyst, but rather selectively stabilizes the charge distribution in the transition state.

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