Nucleophilic Catalysis of Oxime Ligation

Authors

  • Anouk Dirksen Dr.,

    1. Departments of Cell Biology and Chemistry, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7319
    2. Cardiovascular Research Institute Maastricht, University Maastricht, P.O. Box 616, 6200 MD Maastricht, The Netherlands
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  • Tilman M. Hackeng Dr.,

    1. Cardiovascular Research Institute Maastricht, University Maastricht, P.O. Box 616, 6200 MD Maastricht, The Netherlands
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  • Philip E. Dawson Dr.

    1. Departments of Cell Biology and Chemistry, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-7319
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  • This work was supported by the Netherlands Organization for Scientific Research (NWO; to A.D.) and by the National Institutes of Health (GM059380 to P.E.D.).

Abstract

original image

Aniline acts as a nucleophilic catalyst of oxime ligation in aqueous solution through formation of the orange-colored intermediate. The method is demonstrated by acceleration of the oxime ligation of peptides at pH 4.5 and pH 7, which extends the scope of this reaction to conditions relevant for the bioconjugation of macromolecules (see scheme).

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