Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000832.1:
Cluster 1Saccharide / Other132944

BGC0000832, clorobiocin biosynthetic gene cluster from Streptomyces roseochromogenes. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: clorobiocin
PubChem ID: 54706138
SMILES string: Copy to clipboard
Molecular formula: C35H37ClN2O11
Average molecular mass: 697.134 Da
Molecular activity: Antibacterial
Molecular target: GyrB, subunit B protein of DNA gyrase

Class-specific details

Biosynthetic class(es):
Saccharide / Other
Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAN65229.1:
Specificity: L-noviose
Evidence for specificity: Sequence-based prediction
Sugar biosynthesis subcluster: AAN65241.1, AAN65242.1, AAN65243.1, AAN65244.1, AAN65245.1
Other biosynthetic class:
Aminocoumarin

Gene cluster description

clorobiocin (BGC0000832). Gene Cluster 1. Biosynthetic class = Saccharide/Other. GenBank AF329398, positions 9348-42291. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays, Heterologous expression, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Alexander Kristian Apel (Eberhard Karls Universitaet Tuebingen)

Literature references

1. Pojer F et al. (2002) Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology 148(Pt 12):3901-11. doi: 10.1099/00221287-148-12-3901.
2. Schmutz E et al. (2003) Resistance genes of aminocoumarin producers: two type II topoisomerase genes confer resistance against coumermycin A1 and clorobiocin. Antimicrob Agents Chemother 47(3):869-77.
3. Eustaquio AS et al. (2003) Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs. Chem Biol 10(3):279-88.
4. Freitag A et al. (2005) Metabolic engineering of aminocoumarins: inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host. Chembiochem 6(8):1411-8. doi: 10.1002/cbic.200500019.
5. Eustaquio AS et al. (2005) Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters. Appl Environ Microbiol 71(5):2452-9. doi:
6. Garneau S et al. (2005) Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Biochemistry 44(8):2770-80. doi: 10.1021/bi0476329.
7. Xu H et al. (2003) CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin. Microbiology 149(Pt 8):2183-91. doi: 10.1099/mic.0.26314-0.
8. Westrich L et al. (2003) CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin. Chembiochem 4(8):768-73. doi: 10.1002/cbic.200300609.
9. Pojer F et al. (2003) CloR, a bifunctional non-heme iron oxygenase involved in clorobiocin biosynthesis. J Biol Chem 278(33):30661-8. doi: 10.1074/jbc.M303190200. Epub 2003
10. Wolpert M et al. (2007) Effects of deletions of mbtH-like genes on clorobiocin biosynthesis in Streptomyces coelicolor. Microbiology 153(Pt 5):1413-23. doi: 10.1099/mic.0.2006/002998-0.
11. Anderle C et al. (2007) Biosynthesis of clorobiocin: investigation of the transfer and methylation of the pyrrolyl-2-carboxyl moiety. Arch Microbiol 187(3):227-37. doi: 10.1007/s00203-006-0190-9. Epub 2006
12. Keller S et al. (2006) Crystallization and preliminary X-ray analysis of the aromatic prenyltransferase CloQ from the clorobiocin biosynthetic cluster of Streptomyces roseochromogenes. Acta Crystallogr Sect F Struct Biol Cryst Commun 62(Pt 11):1153-5.
13. Freitag A et al. (2006) Biosynthesis of the unusual 5,5-gem-dimethyl-deoxysugar noviose: investigation of the C-methyltransferase gene cloU. Microbiology 152(Pt 8):2433-42. doi: 10.1099/mic.0.28931-0.
14. Garneau-Tsodikova S et al. (2006) Installation of the pyrrolyl-2-carboxyl pharmacophore by CouN1 and CouN7 in the late biosynthetic steps of the aminocoumarin antibiotics clorobiocin and coumermycin A1. Biochemistry 45(28):8568-78. doi: 10.1021/bi060784e.
15. Freitag A et al. (2005) Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar. Chembiochem 6(12):2316-25. doi: 10.1002/cbic.200500252.
16. Fridman M et al. (2007) Chemoenzymatic formation of novel aminocoumarin antibiotics by the enzymes CouN1 and CouN7. Biochemistry 46(28):8462-71. doi: 10.1021/bi700433v. Epub 2007 Jun
17. Ruckert C et al. (2014) Draft Genome Sequence of Streptomyces roseochromogenes subsp. oscitans DS 12.976, Producer of the Aminocoumarin Antibiotic Clorobiocin. LID - 10.1128/genomeA.01147-13 [doi] LID - e01147-13 [pii] Genome Announc 2(1). pii: 2/1/e01147-13. doi:
18. Boll B et al. (2011) Role of MbtH-like proteins in the adenylation of tyrosine during aminocoumarin and vancomycin biosynthesis. J Biol Chem 286(42):36281-90. doi: 10.1074/jbc.M111.288092. Epub
19. Metzger U et al. (2010) Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway. J Mol Biol 404(4):611-26. doi: 10.1016/j.jmb.2010.09.067. Epub 2010