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Chemical Compound Review

Chlorobiocin     [6-[8-chloro-2-hydroxy-3-[[4- hydroxy-3-(3...

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Disease relevance of Chlorobiocin

  • In the present study, the prenyltransferase involved in the biosynthesis of this moiety was identified from the clorobiocin producer (Streptomyces roseochromogenes), overexpressed, and purified [1].
  • Clorobiocin was the most active compound both against E. coli DNA gyrase in vitro and against bacterial growth [2].
  • Twenty-eight novel clorobiocin derivatives obtained from mutasynthesis experiments were investigated for their inhibitory activity towards Escherichia coli DNA gyrase and for their antibacterial activities towards clinically relevant gram-positive and gram-negative bacteria in comparison to novobiocin and clorobiocin [2].
  • Antibacterial activity tests against Bacillus subtilis showed that novclobiocin 109 and novclobiocin 110 have antibacterial activities about eight times less than that of clorobiocin, whereas novclobiocin 104 showed no activity under the test conditions [3].

High impact information on Chlorobiocin


Chemical compound and disease context of Chlorobiocin


Biological context of Chlorobiocin


Associations of Chlorobiocin with other chemical compounds


Gene context of Chlorobiocin


Analytical, diagnostic and therapeutic context of Chlorobiocin


  1. CloQ, a prenyltransferase involved in clorobiocin biosynthesis. Pojer, F., Wemakor, E., Kammerer, B., Chen, H., Walsh, C.T., Li, S.M., Heide, L. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis. Galm, U., Heller, S., Shapiro, S., Page, M., Li, S.M., Heide, L. Antimicrob. Agents Chemother. (2004) [Pubmed]
  3. CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin. Westrich, L., Heide, L., Li, S.M. Chembiochem (2003) [Pubmed]
  4. CloR, a bifunctional non-heme iron oxygenase involved in clorobiocin biosynthesis. Pojer, F., Kahlich, R., Kammerer, B., Li, S.M., Heide, L. J. Biol. Chem. (2003) [Pubmed]
  5. In vitro and in vivo production of new aminocoumarins by a combined biochemical, genetic, and synthetic approach. Galm, U., Dessoy, M.A., Schmidt, J., Wessjohann, L.A., Heide, L. Chem. Biol. (2004) [Pubmed]
  6. Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs. Eustáquio, A.S., Gust, B., Luft, T., Li, S.M., Chater, K.F., Heide, L. Chem. Biol. (2003) [Pubmed]
  7. Structure-Activity Relationships of Aminocoumarin-Type Gyrase and Topoisomerase IV Inhibitors Obtained by Combinatorial Biosynthesis. Flatman, R.H., Eustaquio, A., Li, S.M., Heide, L., Maxwell, A. Antimicrob. Agents Chemother. (2006) [Pubmed]
  8. Installation of the pyrrolyl-2-carboxyl pharmacophore by CouN1 and CouN7 in the late biosynthetic steps of the aminocoumarin antibiotics clorobiocin and coumermycin A1. Garneau-Tsodikova, S., Stapon, A., Kahne, D., Walsh, C.T. Biochemistry (2006) [Pubmed]
  9. Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth. Hooper, D.C., Wolfson, J.S., McHugh, G.L., Winters, M.B., Swartz, M.N. Antimicrob. Agents Chemother. (1982) [Pubmed]
  10. New aminocoumarin antibiotics from a cloQ-defective mutant of the clorobiocin producer Streptomyces roseochromogenes DS12.976. Freitag, A., Galm, U., Li, S.M., Heide, L. J. Antibiot. (2004) [Pubmed]
  11. Metabolic engineering of the heterologous production of clorobiocin derivatives and elloramycin in Streptomyces coelicolor M512. Freitag, A., M??ndez, C., Salas, J.A., Kammerer, B., Li, S.M., Heide, L. Metab. Eng. (2006) [Pubmed]
  12. The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Tsai, F.T., Singh, O.M., Skarzynski, T., Wonacott, A.J., Weston, S., Tucker, A., Pauptit, R.A., Breeze, A.L., Poyser, J.P., O'Brien, R., Ladbury, J.E., Wigley, D.B. Proteins (1997) [Pubmed]
  13. Curing effect of clorobiocin on Escherichia coli plasmids. Cejka, K., Holubová, I., Hubácek, J. Mol. Gen. Genet. (1982) [Pubmed]
  14. Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar. Freitag, A., Wemakor, E., Li, S.M., Heide, L. Chembiochem (2005) [Pubmed]
  15. Correlation of hydrophobicity with protein binding for clorobiocin analogs. Coulson, C.J., Smith, V.J. Journal of pharmaceutical sciences. (1980) [Pubmed]
  16. Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters. Eustáquio, A.S., Gust, B., Galm, U., Li, S.M., Chater, K.F., Heide, L. Appl. Environ. Microbiol. (2005) [Pubmed]
  17. Identification of a topoisomerase IV in actinobacteria: purification and characterization of ParYR and GyrBR from the coumermycin A1 producer Streptomyces rishiriensis DSM 40489. Schmutz, E., Hennig, S., Li, S.M., Heide, L. Microbiology (Reading, Engl.) (2004) [Pubmed]
  18. Envelope protein synthesis and inhibition of cell division in Escherichia coli during inactivation of the B subunit of DNA gyrase. Herrero, E., Fairweather, N.F., Holland, I.B. J. Gen. Microbiol. (1982) [Pubmed]
  19. Inhibition of deoxyribonucleic acid gyrase: effects on nucleic acid synthesis and cell division in Escherichia coli K-12. Fairweather, N.F., Orr, E., Holland, I.B. J. Bacteriol. (1980) [Pubmed]
  20. DNA gyrase interaction with coumarin-based inhibitors: the role of the hydroxybenzoate isopentenyl moiety and the 5'-methyl group of the noviose. Lafitte, D., Lamour, V., Tsvetkov, P.O., Makarov, A.A., Klich, M., Deprez, P., Moras, D., Briand, C., Gilli, R. Biochemistry (2002) [Pubmed]
  21. Metabolic engineering of aminocoumarins: inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host. Freitag, A., Rapp, H., Heide, L., Li, S.M. Chembiochem (2005) [Pubmed]
  22. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Pojer, F., Li, S.M., Heide, L. Microbiology (Reading, Engl.) (2002) [Pubmed]
  23. Crystallization and preliminary X-ray analysis of the aromatic prenyltransferase CloQ from the clorobiocin biosynthetic cluster of Streptomyces roseochromogenes. Keller, S., Pojer, F., Heide, L., Lawson, D.M. Acta Crystallograph. Sect. F Struct. Biol. Cryst. Commun. (2006) [Pubmed]
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