Reports

Methanobactin, a Copper-Acquisition Compound from Methane-Oxidizing Bacteria

Hyung J. Kim,^1* David W. Graham,¹ Alan A. DiSpirito,⁵ Michail A. Alterman,² Nadezhda Galeva,³ Cynthia K. Larive,⁴ Dan Asunskis,⁶ Peter M. A. Sherwood⁶

Siderophores are extracellular iron-binding compounds that mediate iron transport into many cells. We present evidence of analogous molecules for copper transport from methane-oxidizing bacteria, represented here by a small fluorescent chromopeptide (C₄₅N₁₂O₁₄H₆₂Cu, 1216 daltons) produced by Methylosinus trichosporium OB3b. The crystal structure of this compound, methanobactin, was resolved to 1.15 angstroms. It is composed of a tetrapeptide, a tripeptide, and several unusual moieties, including two 4-thionyl-5-hydroxy-imidazole chromophores that coordinate the copper, a pyrrolidine that confers a bend in the overall chain, and an amino-terminal isopropylester group. The copper coordination environment includes a dual nitrogen- and sulfur-donating system derived from the thionyl imidazolate moieties. Structural elucidation of this molecule has broad implications in terms of organo-copper chemistry, biological methane oxidation, and global carbon cycling.

¹ Department of Civil, Environmental, and Architectural Engineering, University of Kansas, Lawrence, KS 66045, USA.
² Biochemical Research Service Laboratory, University of Kansas, Lawrence, KS 66045, USA.
³ Mass Spectrometry Laboratory, University of Kansas, Lawrence, KS 66045, USA.
⁴ Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA.
⁵ Department of Biochemistry, Biophysics, and Molecular Biology, Iowa State University, Ames, IA 50011, USA.
⁶ Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA.

^* Present address: Department of Biochemistry, Molecular Biology, and Biophysics, University of Minnesota, St. Paul, MN 55108, USA.

To whom correspondence should be addressed. E-mail: dwgraham{at}ku.edu

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Two isozymes of particulate methane monooxygenase with different methane oxidation kinetics are found in Methylocystis sp. strain SC2.

M. Baani and W. Liesack (2008)
PNAS 105, 10203-10208
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An Oxidized Tryptophan Facilitates Copper Binding in Methylococcus capsulatus-secreted Protein MopE.

R. Helland, A. Fjellbirkeland, O. A. Karlsen, T. Ve, J. R. Lillehaug, and H. B. Jensen (2008)
J. Biol. Chem. 283, 13897-13904
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From the Cover: Methane monooxygenase gene expression mediated by methanobactin in the presence of mineral copper sources.

C. W. Knapp, D. A. Fowle, E. Kulczycki, J. A. Roberts, and D. W. Graham (2007)
PNAS 104, 12040-12045
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Metabolism of Thioamides by Ralstonia pickettii TA.

A. G. Dodge, J. E. Richman, G. Johnson, and L. P. Wackett (2006)
Appl. Envir. Microbiol. 72, 7468-7476
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Mitochondrial Matrix Copper Complex Used in Metallation of Cytochrome Oxidase and Superoxide Dismutase.

P. A. Cobine, F. Pierrel, M. L. Bestwick, and D. R. Winge (2006)
J. Biol. Chem. 281, 36552-36559
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Duplication of the mmoX gene in Methylosinus sporium: cloning, sequencing and mutational analysis..

H. Ali, J. Scanlan, M. G. Dumont, and J. C. Murrell (2006)
Microbiology 152, 2931-2942
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Evidence of Intense Archaeal and Bacterial Methanotrophic Activity in the Black Sea Water Column.

E. Durisch-Kaiser, L. Klauser, B. Wehrli, and C. Schubert (2005)
Appl. Envir. Microbiol. 71, 8099-8106
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Effect of methanobactin on the activity and electron paramagnetic resonance spectra of the membrane-associated methane monooxygenase in Methylococcus capsulatus Bath.

D. W. Choi, W. E. Antholine, Y. S. Do, J. D. Semrau, C. J. Kisting, R. C. Kunz, D. Campbell, V. Rao, S. C. Hartsel, and A. A. DiSpirito (2005)
Microbiology 151, 3417-3426
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