Petrobactin, a photoreactive siderophore produced by the oil-degrading marine bacterium Marinobacter hydrocarbonoclasticus

J Am Chem Soc. 2002 Jan 23;124(3):378-9. doi: 10.1021/ja0119088.

Abstract

Petrobactin is a bis-catecholate, alpha-hydroxy acid siderophore produced by the oil-degrading marine bacterium Marinobacter hydrocarbonoclasticus. The Fe(III)-complexed form of petrobactin is photoreactive in natural sunlight, mediated by the Fe(III)-citrate moiety. The reaction results in decarboxylation of the petrobactin ligand and reduction of Fe(III) to Fe(II). This report is one of the first to show the photoreactivity of Fe(III)-siderophores mediated by the ferric ion-alpha-hydroxy acid group. The demonstration of light-mediated decarboxylation of an Fe(III)-siderophore complex raises questions about a possible functional role for photoreactivity in siderophore-mediated iron uptake.

Publication types

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

MeSH terms

  • Benzamides*
  • Gammaproteobacteria / chemistry
  • Gammaproteobacteria / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Nuclear Magnetic Resonance, Biomolecular
  • Petroleum / metabolism*
  • Siderophores / biosynthesis
  • Siderophores / chemistry*
  • Siderophores / metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Benzamides
  • Petroleum
  • Siderophores
  • petrobactin