Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000833.1:
Cluster 1Saccharide / Other137834

BGC0000833, coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Coumermycin A1
PubChem ID: 54720057
SMILES string: Copy to clipboard
Molecular formula: C55H59N5O20
Average molecular mass: 1110.092 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:
AAG29785.1:
Specificity: L-noviose
Evidence for specificity: Sequence-based prediction
Sugar biosynthesis subcluster: AAG29801.1, AAG29802.1, AAG29803.1, AAG29804.1, AAG29805.1,
Other biosynthetic class:
Aminocoumarin

Gene cluster description

coumermycin A1 (BGC0000833). Gene Cluster 1. Biosynthetic class = Saccharide/Other. GenBank AF235050, positions 2307-40140. 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. KAWAGUCHI H et al. (1965) STUDIES ON COUMERMYCIN. A NEW ANTIBIOTIC. II. STRUCTURE OF COUMERMYCIN A1. J Antibiot (Tokyo) 18:11-25.
2. KAWAGUCHI H et al. (1965) STUDIES ON COUMERMYCIN, A NEW ANTIBIOTIC. I. PRODUCTION, ISOLATION AND CHARACTERIZATION OF COUMERMYCIN A1. J Antibiot (Tokyo) 18:1-10.
3. Scannell J, Kong YL. (1969 TI) Biosynthesis of coumermycin A1: incorporation of L-proline into the pyrrole groups. Antimicrob Agents Chemother (Bethesda) 9:139-43.
4. Li SM et al. (2002) Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments. Microbiology 148(Pt 10):3317-26. doi: 10.1099/00221287-148-10-3317.
5. Wang ZX et al. (2000) Identification of the coumermycin A(1) biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Antimicrob Agents Chemother 44(11):3040-8.
6. Freel Meyers CL et al. (2004) Assembly of dimeric variants of coumermycins by tandem action of the four biosynthetic enzymes CouL, CouM, CouP, and NovN. Biochemistry 43(47):15022-36. doi: 10.1021/bi048457z.
7. Schmutz E et al. (2004) Identification of a topoisomerase IV in actinobacteria: purification and characterization of ParYR and GyrBR from the coumermycin A1 producer Streptomyces rishiriensis DSM 40489. Microbiology 150(Pt 3):641-7. doi: 10.1099/mic.0.26867-0.
8. Galm U et al. (2004) In vitro and in vivo production of new aminocoumarins by a combined biochemical, genetic, and synthetic approach. Chem Biol 11(2):173-83. doi: 10.1016/j.chembiol.2004.01.012.
9. Schmutz E et al. (2003) An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489. Eur J Biochem 270(22):4413-9.
10. 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.
11. Xu H et al. (2002) Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin. Mol Genet Genomics 268(3):387-96. doi: 10.1007/s00438-002-0759-1. Epub
12. 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.
13. Pacholec M et al. (2005) CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis. Biochemistry 44(45):14969-76. doi: 10.1021/bi051599o.
14. 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.
15. Wolpert M et al. (2008) Assembly and heterologous expression of the coumermycin A1 gene cluster and production of new derivatives by genetic engineering. Chembiochem 9(4):603-12. doi: 10.1002/cbic.200700483.
16. Balibar CJ et al. (2007) Covalent CouN7 enzyme intermediate for acyl group shuttling in aminocoumarin biosynthesis. Chem Biol 14(6):679-90. doi: 10.1016/j.chembiol.2007.05.007.
17. 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
18. Novotna J et al. (2013) Five gene products are required for assembly of the central pyrrole moiety of coumermycin A1. J Ind Microbiol Biotechnol 40(8):915-25. doi:
19. Siebenberg S et al. (2011) Two pathways for pyrrole formation in coumermycin A(1) biosynthesis: the central pyrrole moiety is formed from L-threonine. Chembiochem 12(17):2677-85. doi: 10.1002/cbic.201100494. Epub 2011