BGC0000833

BGC0000833: coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis

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Location: 2,307 - 40,140 nt. (total: 37,834 nt).
This entry is originally from NCBI GenBank AF235050.4.

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core biosynthetic genes

additional biosynthetic genes

transport-related genes

regulatory genes

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resistance

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Gene details

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General

Compounds

Genes

Biosynthesis

History

KnownClusterBlast

General information about the BGC

MIBiG accession	BGC0000833
Short description	coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis
Status	Quality: questionable The quality level of this entry. Status: active The status of this entry. Completeness: complete Whether the entry covers everything needed for the pathway producing the compound(s)
Biosynthetic class(es)	saccharide (hybrid/tailoring) other (aminocoumarin)
Loci	AF235050.4 2307 - 40140 via Knock-out studies, Enzymatic assays, Heterologous expression
Compounds	coumermycin A1
Species	Streptomyces rishiriensis [taxonomy]
References	[1] Identification of the coumermycin A(1) biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Wang ZX et al., Antimicrob Agents Chemother (2000) PMID:11036020 [2] Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments. Li SM et al., Microbiology (Reading) (2002) PMID:12368465 [3] Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin. Xu H et al., Mol Genet Genomics (2002) PMID:12436260 [4] Resistance genes of aminocoumarin producers: two type II topoisomerase genes confer resistance against coumermycin A1 and clorobiocin. Schmutz E et al., Antimicrob Agents Chemother (2003) PMID:12604514 [5] STUDIES ON COUMERMYCIN. A NEW ANTIBIOTIC. II. STRUCTURE OF COUMERMYCIN A1. KAWAGUCHI H et al., J Antibiot (Tokyo) (1965) PMID:14285468 [6] STUDIES ON COUMERMYCIN, A NEW ANTIBIOTIC. I. PRODUCTION, ISOLATION AND CHARACTERIZATION OF COUMERMYCIN A1. KAWAGUCHI H et al., J Antibiot (Tokyo) (1965) PMID:14285469 [7] An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489. Schmutz E et al., Eur J Biochem (2003) PMID:14622269 [8] 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 et al., Microbiology (Reading) (2004) PMID:14993313 [9] In vitro and in vivo production of new aminocoumarins by a combined biochemical, genetic, and synthetic approach. Galm U et al., Chem Biol (2004) PMID:15123279 [10] Assembly of dimeric variants of coumermycins by tandem action of the four biosynthetic enzymes CouL, CouM, CouP, and NovN. Freel Meyers CL et al., Biochemistry (2004) PMID:15554710 [11] Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Garneau S et al., Biochemistry (2005) PMID:15723521 [12] CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis. Pacholec M et al., Biochemistry (2005) PMID:16274243 [13] 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 et al., Biochemistry (2006) PMID:16834331 [14] Chemoenzymatic formation of novel aminocoumarin antibiotics by the enzymes CouN1 and CouN7. Fridman M et al., Biochemistry (2007) PMID:17580964 [15] Covalent CouN7 enzyme intermediate for acyl group shuttling in aminocoumarin biosynthesis. Balibar CJ et al., Chem Biol (2007) PMID:17584615 [16] Assembly and heterologous expression of the coumermycin A1 gene cluster and production of new derivatives by genetic engineering. Wolpert M et al., Chembiochem (2008) PMID:18288655 [17] Two pathways for pyrrole formation in coumermycin A(1) biosynthesis: the central pyrrole moiety is formed from L-threonine. Siebenberg S et al., Chembiochem (2011) PMID:21953874 [18] Five gene products are required for assembly of the central pyrrole moiety of coumermycin A1. Novotna J et al., J Ind Microbiol Biotechnol (2013) PMID:23652970 [19] Biosynthesis of coumermycin A1: incorporation of L-proline into the pyrrole groups. Scannell J et al., Antimicrob Agents Chemother (Bethesda) (1969) PMID:5396481

Chemical products information

coumermycin A1 Evidence:

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C₅₅H₅₉N₅O₂₀

Chemical database entries
PubCHEM
PubCHEM

List of genes involved in compound(s) production

Identifiers	Position	Product	Functions	Evidence	Extra
AAR11885.1 couE	2307 - 2960 (+)	regulatory protein CouE	Regulation		copy AA seq copy Nt seq
AAG29778.1 couG	4114 - 5073 (+)	regulatory protein CouG	Regulation		copy AA seq copy Nt seq
AAG29779.1 couY	5410 - 5625 (+)	mbtH-like protein	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29780.1 couH	5931 - 7730 (+)	peptide synthetase-like protein	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29781.1 couI	7734 - 8957 (+)	cytochrome P450	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29782.1 couJ	9117 - 9893 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29783.1 couK	9890 - 10627 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29784.2 couL	10634 - 12223 (+)	amide synthetase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAG29785.1 couM	12237 - 13445 (+)	glycosyltransferase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAG29786.1 couN1	13526 - 13813 (+)	acyl carrier protein	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAG29787.2 couN2	13824 - 14891 (+)	acyltransferase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29788.2 couN3	14881 - 16011 (+)	acyl-CoA dehydrogenase	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAG29789.1 couN4	16130 - 17635 (+)	acyl-CoA synthetase	Scaffold biosynthesis	Knock-out Activity assay	copy AA seq copy Nt seq
AAG29790.1 couN5	17639 - 17908 (+)	acyl carrier protein	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAG29791.2 couN6	17966 - 19648 (+)	methyltransferase	Tailoring		copy AA seq copy Nt seq
AAG29792.1 couN7	19697 - 20542 (+)	acyltransferase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAG29793.1 couO	20892 - 21584 (+)	methyltransferase	Tailoring	Knock-out Activity assay	copy AA seq copy Nt seq
AAG29794.1 couP	21984 - 22814 (+)	O-methyltransferase	Tailoring	Knock-out Activity assay	copy AA seq copy Nt seq
AAG29795.1 couR1	22911 - 24335 (+)	tryptophan synthase b-subunit-like\nPLP-dependent enzyme	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AEO99210.1 couR2a	24335 - 24853 (+)	decarboxylase subunit	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AEO99211.1 couR2b	24850 - 25467 (+)	decarboxylase subunit	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAG29797.1 couR3	25500 - 26408 (+)	threonine kinase	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAG29798.1 couR4	26463 - 27632 (+)	FMN-dependent dehydrogenases	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAG29799.1 couR5	27686 - 29161 (-)	putative resistance protein, transporter	Resistance/immunity		copy AA seq copy Nt seq
AAG29800.2 couR6	29296 - 30171 (+)	regulatory protein	Regulation		copy AA seq copy Nt seq
AAG29801.1 couS	30425 - 31291 (+)	dTDP-4-keto-6-deoxyhexose reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29802.1 couT	31325 - 32335 (+)	dTDP-glucose 4,6-dehydratase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29803.1 couU	32561 - 33823 (+)	C-methyltransferase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29804.1 couV	33882 - 34772 (+)	dTDP-glucose synthase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAG29805.1 couW	34769 - 35365 (+)	dTDP-4-keto-6-deoxyglucose 3,5-epimerase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAO47225.2 gyrB-Rc	35917 - 37950 (+)	resistant DNA gyrase subunit B	Resistance/immunity	Activity assay	copy AA seq copy Nt seq
AAO47226.2 parYR	38029 - 40140 (+)	resistant type II topoisomerase subunit B	Resistance/immunity	Activity assay	copy AA seq copy Nt seq

Biosynthesis information

Annotation changelog

Entry version: 3

Date

Changes

Submitters

Reviewers

2022-10-07

Update chemical activity to schema version 2.11

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Entry version: 2

Date

Changes

Submitters

Reviewers

2019-10-16

Migrated from v1.4

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2019-10-16

Updated compound(s) information (MIBiG Annotathon)

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2019-10-16

Updated compound(s) information (NPAtlas curation)

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Entry version: 1

Date

Changes

Submitters

Reviewers

2015-06-12

Submitted

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