Abstract

Genome mining and chemical analyses revealed that rhizosphere bacteria (Paraburkholderia graminis) produce a new type of siderophore, gramibactin, a lipodepsipeptide that efficiently binds iron with a logβ value of 27.6. Complexation-induced proton NMR chemical shifts show that the unusual N-nitrosohydroxylamine (diazeniumdiolate) moieties participate in metal binding. Gramibactin biosynthesis genes are conserved in numerous plant-associated bacteria associated with rice, wheat, and maize, which may utilize iron from the complex.

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Acknowledgements

We thank A. Perner for MS analyses and H. Heinecke for NMR measurements. We thank D. Milea for helpful discussion on thermodynamic data and M. Frontauria for potentiometric titrations. We thank the Deutsche Forschungsgemeinschaft for financial support (SFB 1127, ChemBioSys, and Leibniz Award to C.H.).

Author information

Affiliations

  1. Department of Biomolecular Chemistry, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Jena, Germany

    • Ron Hermenau
    • , Keishi Ishida
    •  & Christian Hertweck
  2. Institute for Inorganic and Analytical Chemistry, Friedrich Schiller University, Jena, Germany

    • Sofia Gama
    • , Winfried Plass
    • , Jan Frieder Mohr
    •  & Thomas Wichard
  3. Department of Cell and Molecular Biology, Leibniz Institute for Natural Product Research and Infection Biology (HKI), Jena, Germany

    • Bianca Hoffmann
    • , Michel Pfeifer-Leeg
    •  & Hans-Peter Saluz
  4. Friedrich Schiller University, Faculty of Biology and Pharmacy, Jena, Germany

    • Hans-Peter Saluz
    •  & Christian Hertweck

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Contributions

R.H., K.I. and C.H. designed experiments; R.H. conducted cultivation, isolation and structure elucidation experiments, synthesized reference compounds and performed all experiments involving corn plants. K.I. performed genetic experiments; R.H. and K.I. performed bioinformatic analyses and analyzed data. R.H. and M.P.-L. prepared radioisotope complexes. B.H. designed and performed PET–CT experiments and analyzed resulting data. W.P. and S.G. designed thermodynamic studies, R.H. and S.G. performed titrations and S.G. calculated physicochemical constants. J.F.M. performed AAS measurements. T.W. supervised, organized and discussed results concerning iron quantification using AAS. H.-P.S. supervised, organized and discussed results concerning radiochemistry and PET–CT imaging. R.H. and C.H. wrote the manuscript.

Competing interests

The authors declare no competing interests.

Corresponding author

Correspondence to Christian Hertweck.

Supplementary information

  1. Supplementary Text and Figures

    Supplementary Tables 1–6, Supplementary Figures 1–14

  2. Reporting Summary

  3. Supplementary Note 1

    Synthetic Procedures

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DOI

https://doi.org/10.1038/s41589-018-0101-9