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Nitro versus Hydroxamate in Siderophores of Pathogenic Bacteria: Effect of Missing Hydroxylamine Protection in Malleobactin Biosynthesis

Authors

  • Jakob Franke,

    1. Dept. of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena (Germany)
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    • These authors contributed equally to this work.

  • Dr. Keishi Ishida,

    1. Dept. of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena (Germany)
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    • These authors contributed equally to this work.

  • Dr. Mie Ishida-Ito,

    1. Dept. of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena (Germany)
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  • Prof. Dr. Christian Hertweck

    Corresponding author
    1. Dept. of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena (Germany)
    2. Friedrich Schiller University, Jena (Germany)
    • Dept. of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena (Germany)
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  • We thank A. Perner and H. Heinecke for MS and NMR measurements. This work was supported by the “Pakt für Forschung und Innovation” of the Free State of Thuringia and the BMBF.

Abstract

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Die langgesuchte Struktur von Malleobactin, einem Virulenzfaktor von Pathogenen der Familie Burkholderia mallei, wurde durch genetische und chemische Analysen aufgeklärt. Der neue nitrosubstituierte Siderophor ist von einem ungewöhnlichen ungeschützten Hydroxylamin abgeleitet, das spontane Oxidation erfährt, wie in In-vitro-Assays und durch Nachweis von Analoga mit Hydroxylamin-, Nitroso- und Azoxid-Gruppen gezeigt wurde.

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