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Chemical Compound Review

Corynebactin     N-[[(2R,3S,6R,7S,10R,11S)- 7,11-bis[2-[(2,3...

Synonyms: Bacillibactin, CPD-9984, CHEBI:31432, AC1L2OG5, C12219, ...
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Disease relevance of C12219


High impact information on C12219

  • Despite the great efficiency of BB at chelating iron, PB may be the only siderophore necessary to ensure full virulence of the pathogen [5].
  • The synthesis of the catecholic siderophore bacillibactin is accomplished by the nonribosomal peptide synthetase (NRPS) encoded by the dhb operon [6].
  • Upon iron limitation, Bacillus subtilis secretes the catecholic trilactone (2,3-dihydroxybenzoate-glycine-threonine)(3) siderophore bacillibactin (BB) for ferric iron scavenging [7].
  • A clone of the wild-type irp6 operon (pCM6ABC) complemented the constitutive corynebactin production phenotype of HC1, HC4, and HC5 but not of HC3, whereas a clone of the wild-type irp1 operon failed to complement any of these strains [8].
  • Three Bacillus anthracis Sterne strains (USAMRIID, 7702, and 34F2) and Bacillus cereus ATCC 14579 excrete two catecholate siderophores, petrobactin (which contains 3,4-dihydroxybenzoyl moieties) and bacillibactin (which contains 2,3-dihydroxybenzoyl moieties) [4].

Associations of C12219 with other chemical compounds

  • The chirality and relative conformational stability of the three ferric complexes of enterobactin, corynebactin, and the hybrid have been investigated by molecular modeling (including MM3 and pBP86/DN density functional theory calculations) and circular dichroism spectra [9].

Analytical, diagnostic and therapeutic context of C12219

  • The present microarray analysis of iron-starved Bacillus subtilis cells grown in minimal medium unveils additional physiological effects on a large number of genes linked to stringent-response regulation and to genes involved in amino acid biosynthesis associated with pathways essential for bacillibactin production [10].


  1. The dhb operon of Bacillus subtilis encodes the biosynthetic template for the catecholic siderophore 2,3-dihydroxybenzoate-glycine-threonine trimeric ester bacillibactin. May, J.J., Wendrich, T.M., Marahiel, M.A. J. Biol. Chem. (2001) [Pubmed]
  2. Siderophore-mediated iron transport in Bacillus subtilis and Corynebacterium glutamicum. Dertz, E.A., Stintzi, A., Raymond, K.N. J. Biol. Inorg. Chem. (2006) [Pubmed]
  3. The Bordetella bfe system: growth and transcriptional response to siderophores, catechols, and neuroendocrine catecholamines. Anderson, M.T., Armstrong, S.K. J. Bacteriol. (2006) [Pubmed]
  4. Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis. Wilson, M.K., Abergel, R.J., Raymond, K.N., Arceneaux, J.E., Byers, B.R. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  5. Anthrax pathogen evades the mammalian immune system through stealth siderophore production. Abergel, R.J., Wilson, M.K., Arceneaux, J.E., Hoette, T.M., Strong, R.K., Byers, B.R., Raymond, K.N. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  6. Crystal structure of DhbE, an archetype for aryl acid activating domains of modular nonribosomal peptide synthetases. May, J.J., Kessler, N., Marahiel, M.A., Stubbs, M.T. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  7. Ferri-bacillibactin uptake and hydrolysis in Bacillus subtilis. Miethke, M., Klotz, O., Linne, U., May, J.J., Beckering, C.L., Marahiel, M.A. Mol. Microbiol. (2006) [Pubmed]
  8. Identification of a DtxR-regulated operon that is essential for siderophore-dependent iron uptake in Corynebacterium diphtheriae. Qian, Y., Lee, J.H., Holmes, R.K. J. Bacteriol. (2002) [Pubmed]
  9. Corynebactin and a serine trilactone based analogue: chirality and molecular modeling of ferric complexes. Bluhm, M.E., Hay, B.P., Kim, S.S., Dertz, E.A., Raymond, K.N. Inorganic chemistry. (2002) [Pubmed]
  10. Iron Starvation Triggers the Stringent Response and Induces Amino Acid Biosynthesis for Bacillibactin Production in Bacillus subtilis. Miethke, M., Westers, H., Blom, E.J., Kuipers, O.P., Marahiel, M.A. J. Bacteriol. (2006) [Pubmed]
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