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Characterization of a Copper-Chelating Natural Product from the Methanotroph Methylosinus sp. LW3

  • Yun Ji Park
    Yun Ji Park
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
    More by Yun Ji Park
  • Gerri M. Roberts
    Gerri M. Roberts
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  • Rana Montaser
    Rana Montaser
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  • Grace E. Kenney
    Grace E. Kenney
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  • Paul M. Thomas
    Paul M. Thomas
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  • Neil L. Kelleher
    Neil L. Kelleher
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
  • , and 
  • Amy C. Rosenzweig*
    Amy C. Rosenzweig
    Departments of Molecular Biosciences and Chemistry, Northwestern University, Evanston, Illinois 60208, United States
    *Email: [email protected]
Cite this: Biochemistry 2021, 60, 38, 2845–2850
Publication Date (Web):September 12, 2021
https://doi.org/10.1021/acs.biochem.1c00443
Copyright © 2021 American Chemical Society

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    Abstract

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    Methanobactins (Mbns) are ribosomally produced, post-translationally modified peptidic natural products that bind copper with high affinity. Methanotrophic bacteria use Mbns to acquire copper needed for enzymatic methane oxidation. Despite the presence of Mbn operons in a range of methanotroph and other bacterial genomes, few Mbns have been isolated and structurally characterized. Here we report the isolation of a novel Mbn from the methanotroph Methylosinus (Ms.) sp. LW3. Mass spectrometric and nuclear magnetic resonance spectroscopic data indicate that this Mbn, the largest characterized to date, consists of a 13-amino acid backbone modified to include pyrazinedione/oxazolone rings and neighboring thioamide groups derived from cysteine residues. The pyrazinedione ring is more stable to acid hydrolysis than the oxazolone ring and likely protects the Mbn from degradation. The structure corresponds exactly to that predicted on the basis of the Ms. sp. LW3 Mbn operon content, providing support for the proposed role of an uncharacterized biosynthetic enzyme, MbnF, and expanding the diversity of known Mbns.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.biochem.1c00443.

    • Experimental methods, figures of Mbn chemical structures, operon groups, and biosynthetic pathway, UV–vis spectra, MS/MS spectra, NMR spectra and couplings, and a table of NMR assignments (PDF)

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    Cited By

    This article is cited by 4 publications.

    1. Frank J. Tucci, Amy C. Rosenzweig. Direct Methane Oxidation by Copper- and Iron-Dependent Methane Monooxygenases. Chemical Reviews 2024, 124 (3) , 1288-1320. https://doi.org/10.1021/acs.chemrev.3c00727
    2. Peng Peng, Wenyu Gu, Alan A. DiSpirito, Jeremy D. Semrau, . Multiple Mechanisms for Copper Uptake by Methylosinus trichosporium OB3b in the Presence of Heterologous Methanobactin. mBio 2022, 13 (5) https://doi.org/10.1128/mbio.02239-22
    3. Zachary L Reitz, Marnix H Medema. Genome mining strategies for metallophore discovery. Current Opinion in Biotechnology 2022, 77 , 102757. https://doi.org/10.1016/j.copbio.2022.102757
    4. Yun Ji Park, Richard J. Jodts, Jeffrey W. Slater, Reyvin M. Reyes, Valerie J. Winton, Rana A. Montaser, Paul M. Thomas, William B. Dowdle, Anahi Ruiz, Neil L. Kelleher, J. Martin Bollinger, Carsten Krebs, Brian M. Hoffman, Amy C. Rosenzweig. A mixed-valent Fe(II)Fe(III) species converts cysteine to an oxazolone/thioamide pair in methanobactin biosynthesis. Proceedings of the National Academy of Sciences 2022, 119 (13) https://doi.org/10.1073/pnas.2123566119