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Science 10 September 2004:
Vol. 305. no. 5690, pp. 1612 - 1615
DOI: 10.1126/science.1098322
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Reports

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

Hyung J. Kim,1* David W. Graham,1{dagger} 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.

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

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