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Chemical Compound Review

Vibriobactin     (2Z,4S,5R)-N-[3-[(2,3- dihydroxyphenyl)carb...

Synonyms: AC1NUWCM, CPD-2002, C06769, 88217-23-6
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Disease relevance of C06769

  • We report the crystal structure of the free-standing NRPS condensation (C) domain VibH, which catalyzes amide bond formation in the synthesis of vibriobactin, a Vibrio cholerae siderophore [1].
  • The six-domain, 270 kDa nonribosomal peptide synthetase (NRPS) VibF, a component of vibriobactin synthetase, has been heterologously expressed in Escherichia coli and purified [2].
  • Finally, vibriobactin is also shown to be active with a human Burkitt lymphoma cell line (Daudi) [3].

High impact information on C06769


Chemical compound and disease context of C06769


Biological context of C06769

  • We have identified genes for vibriobactin transport and mapped them within the vibriobactin biosynthetic gene cluster [8].
  • Chromosomal DNA downstream of the Vibrio cholerae ferric vibriobactin receptor gene, viuA, was cloned and sequenced, revealing an 813-bp open reading frame encoding a deduced protein of 271 amino acids [9].
  • DNA sequences encoding the gene into which TnphoA had inserted, designated viuA (vibriobactin uptake), restored the wild-type phenotype to the mutant; the complemented mutant expressed the 74-kDa outer membrane protein under iron-limiting conditions and possessed normal vibriobactin binding and uptake [10].
  • The microbial iron chelator vibriobactin, N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2, 3-dihydroxyphenyl)-trans-5-methyl-2-oxazoline-4-carboxamido]-propane, is shown to inhibit the growth of L1210 cells in culture, with an IC50 value of 2 microM [3].
  • Furthermore, after exposure of L1210 cells to vibriobactin (10 microM) for 5 hrs followed by removal of the drug, cells display different doubling times relative to untreated controls, with lower bromodeoxyuridine (BrdUrd) incorporation and no apparent cell death as shown by a 51Cr release assay [3].

Gene context of C06769

  • Vibrio cholerae has multiple iron acquisition systems, including TonB-dependent transport of heme and of the catechol siderophore vibriobactin [11].
  • Unexpectedly, hydropathicity analysis of ViuB did not reveal a signal sequence or transmembrane domain, suggesting that ViuB is not a periplasmic or membrane protein but may be a cytoplasmic protein involved in ferric vibriobactin uptake and processing, perhaps analogous to the Escherichia coli protein Fes [9].

Analytical, diagnostic and therapeutic context of C06769


  1. The structure of VibH represents nonribosomal peptide synthetase condensation, cyclization and epimerization domains. Keating, T.A., Marshall, C.G., Walsh, C.T., Keating, A.E. Nat. Struct. Biol. (2002) [Pubmed]
  2. Reconstitution and characterization of the Vibrio cholerae vibriobactin synthetase from VibB, VibE, VibF, and VibH. Keating, T.A., Marshall, C.G., Walsh, C.T. Biochemistry (2000) [Pubmed]
  3. Effects of the Vibrio cholerae siderophore vibriobactin on the growth characteristics of L1210 cells. Bergeron, R.J., Braylan, R., Goldey, S., Ingeno, M. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  4. Vibrio cholerae iron transport: haem transport genes are linked to one of two sets of tonB, exbB, exbD genes. Occhino, D.A., Wyckoff, E.E., Henderson, D.P., Wrona, T.J., Payne, S.M. Mol. Microbiol. (1998) [Pubmed]
  5. Catalytically inactive condensation domain C1 is responsible for the dimerization of the VibF subunit of vibriobactin synthetase. Hillson, N.J., Balibar, C.J., Walsh, C.T. Biochemistry (2004) [Pubmed]
  6. Vibriobactin biosynthesis in Vibrio cholerae: VibH is an amide synthase homologous to nonribosomal peptide synthetase condensation domains. Keating, T.A., Marshall, C.G., Walsh, C.T. Biochemistry (2000) [Pubmed]
  7. Cloning and characterization of vuuA, a gene encoding the Vibrio vulnificus ferric vulnibactin receptor. Webster, A.C., Litwin, C.M. Infect. Immun. (2000) [Pubmed]
  8. A multifunctional ATP-binding cassette transporter system from Vibrio cholerae transports vibriobactin and enterobactin. Wyckoff, E.E., Valle, A.M., Smith, S.L., Payne, S.M. J. Bacteriol. (1999) [Pubmed]
  9. Identification, cloning, and sequencing of a gene required for ferric vibriobactin utilization by Vibrio cholerae. Butterton, J.R., Calderwood, S.B. J. Bacteriol. (1994) [Pubmed]
  10. Identification of the vibriobactin receptor of Vibrio cholerae. Stoebner, J.A., Butterton, J.R., Calderwood, S.B., Payne, S.M. J. Bacteriol. (1992) [Pubmed]
  11. Characterization of ferric and ferrous iron transport systems in Vibrio cholerae. Wyckoff, E.E., Mey, A.R., Leimbach, A., Fisher, C.F., Payne, S.M. J. Bacteriol. (2006) [Pubmed]
  12. Dissection of the EntF condensation domain boundary and active site residues in nonribosomal peptide synthesis. Roche, E.D., Walsh, C.T. Biochemistry (2003) [Pubmed]
  13. Dimeric structure of the six-domain VibF subunit of vibriobactin synthetase: mutant domain activity regain and ultracentrifugation studies. Hillson, N.J., Walsh, C.T. Biochemistry (2003) [Pubmed]
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