Methanobactin, a copper-acquisition compound from methane-oxidizing bacteria

Science. 2004 Sep 10;305(5690):1612-5. doi: 10.1126/science.1098322.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids / analysis
  • Chemical Phenomena
  • Chemistry, Physical
  • Copper / analysis
  • Copper / chemistry
  • Copper / metabolism*
  • Crystallization
  • Crystallography, X-Ray
  • Dimerization
  • Imidazoles / chemistry*
  • Imidazoles / isolation & purification
  • Imidazoles / metabolism
  • Ligands
  • Methane / metabolism
  • Methylosinus trichosporium / chemistry
  • Methylosinus trichosporium / metabolism*
  • Models, Molecular
  • Molecular Structure
  • Molecular Weight
  • Oligopeptides / chemistry*
  • Oligopeptides / isolation & purification
  • Oligopeptides / metabolism
  • Oxidation-Reduction
  • Spectrum Analysis

Substances

  • Amino Acids
  • Imidazoles
  • Ligands
  • Oligopeptides
  • methanobactin
  • Copper
  • Methane