BGC0000832

BGC0000832: clorobiocin biosynthetic gene cluster from Streptomyces roseochromogenus subsp. oscitans DS 12.976

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Location: 9,348 - 42,291 nt. (total: 32,944 nt).
This entry is originally from NCBI GenBank AF329398.1.

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core biosynthetic genes

additional biosynthetic genes

transport-related genes

regulatory genes

other genes

resistance

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Gene details

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General

Compounds

Genes

Biosynthesis

History

KnownClusterBlast

General information about the BGC

MIBiG accession	BGC0000832
Short description	clorobiocin biosynthetic gene cluster from Streptomyces roseochromogenus subsp. oscitans DS 12.976
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	AF329398.1 9348 - 42291 via Knock-out studies, Enzymatic assays, Heterologous expression
Compounds	clorobiocin
Species	Streptomyces roseochromogenus subsp. oscitans DS 12.976 [taxonomy]
References	[1] Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Pojer F et al., Microbiology (Reading) (2002) PMID:12480894 [2] 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 [3] Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs. Eustáquio AS et al., Chem Biol (2003) PMID:12670542 [4] CloR, a bifunctional non-heme iron oxygenase involved in clorobiocin biosynthesis. Pojer F et al., J Biol Chem (2003) PMID:12777382 [5] CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin. Westrich L et al., Chembiochem (2003) PMID:12898629 [6] CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin. Xu H et al., Microbiology (Reading) (2003) PMID:12904558 [7] Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Garneau S et al., Biochemistry (2005) PMID:15723521 [8] Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters. Eustáquio AS et al., Appl Environ Microbiol (2005) PMID:15870333 [9] Metabolic engineering of aminocoumarins: inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host. Freitag A et al., Chembiochem (2005) PMID:15977275 [10] Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar. Freitag A et al., Chembiochem (2005) PMID:16276503 [11] 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 [12] Biosynthesis of the unusual 5,5-gem-dimethyl-deoxysugar noviose: investigation of the C-methyltransferase gene cloU. Freitag A et al., Microbiology (Reading) (2006) PMID:16849806 [13] Crystallization and preliminary X-ray analysis of the aromatic prenyltransferase CloQ from the clorobiocin biosynthetic cluster of Streptomyces roseochromogenes. Keller S et al., Acta Crystallogr Sect F Struct Biol Cryst Commun (2006) PMID:17077503 [14] Biosynthesis of clorobiocin: investigation of the transfer and methylation of the pyrrolyl-2-carboxyl moiety. Anderle C et al., Arch Microbiol (2007) PMID:17308937 [15] Effects of deletions of mbtH-like genes on clorobiocin biosynthesis in Streptomyces coelicolor. Wolpert M et al., Microbiology (Reading) (2007) PMID:17464055 [16] Chemoenzymatic formation of novel aminocoumarin antibiotics by the enzymes CouN1 and CouN7. Fridman M et al., Biochemistry (2007) PMID:17580964 [17] Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway. Metzger U et al., J Mol Biol (2010) PMID:20946900 [18] Role of MbtH-like proteins in the adenylation of tyrosine during aminocoumarin and vancomycin biosynthesis. Boll B et al., J Biol Chem (2011) PMID:21890635 [19] Draft Genome Sequence of Streptomyces roseochromogenes subsp. oscitans DS 12.976, Producer of the Aminocoumarin Antibiotic Clorobiocin. Rückert C et al., Genome Announc (2014) PMID:24407645

Chemical products information

clorobiocin Evidence:

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C₃₅H₃₇Cl₁N₂O₁₁

Chemical database entries
PubCHEM

List of genes involved in compound(s) production

Identifiers	Position	Product	Functions	Evidence	Extra
AAN65220.1 cloE	9348 - 10001 (+)	Regulatory protein CloE	Regulation	Knock-out	copy AA seq copy Nt seq
AAN65221.1 cloF	10078 - 11166 (+)	prephenate dehydrogenase	Precursor biosynthesis		copy AA seq copy Nt seq
AAN65222.1 cloG	11746 - 12705 (+)	regulatory protein CloG	Regulation	Knock-out	copy AA seq copy Nt seq
AAN65223.1 cloY	12920 - 13135 (+)	mbtH-like protein	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65224.1 cloH	13390 - 15192 (+)	peptide synthetase-like protein	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65225.1 cloI	15196 - 16419 (+)	cytochrome P450	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65226.1 cloJ	16573 - 17349 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65227.1 cloK	17346 - 18083 (+)	b-ketotyrosyl-reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65228.1 cloL	18090 - 19673 (+)	amide synthetase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65229.1 cloM	19687 - 20859 (+)	glycosyltransferase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65230.1 cloN1	20853 - 21140 (+)	acyl carrier protein	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAN65231.1 cloN2	21150 - 22217 (+)	acyltransferase	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAN65232.1 cloN3	22207 - 23337 (+)	acyl-CoA dehydrogenase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65233.1 cloN4	23456 - 24961 (+)	acyl-CoA synthetase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65234.1 cloN5	24965 - 25234 (+)	acyl carrier protein	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65235.1 cloN6	25292 - 26977 (+)	methyltransferase	Tailoring	Knock-out	copy AA seq copy Nt seq
AAN65236.1 cloN7	27026 - 27862 (+)	acyl transferase	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAN65237.1 clohal	28099 - 29673 (+)	halogenase	Tailoring	Knock-out	copy AA seq copy Nt seq
AAN65238.1 cloP	29998 - 30831 (+)	O-methyltransferase	Tailoring	Knock-out	copy AA seq copy Nt seq
AAN65239.1 cloQ	31832 - 32806 (+)	ABBA prenyltransferase	Scaffold biosynthesis	Activity assay	copy AA seq copy Nt seq
AAN65240.1 cloR	32803 - 33636 (+)	alpha-ketoacid-dependent oxygenase	Scaffold biosynthesis	Knock-out	copy AA seq copy Nt seq
AAN65241.1 cloS	34466 - 35332 (+)	dTDP-4-keto-6-deoxyhexose reductase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65242.1 cloT	35366 - 36376 (+)	dTDP-glucose 4,6-dehydratase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65243.1 cloU	36602 - 37864 (+)	C-methyltransferase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65244.1 cloV	37976 - 38866 (+)	dTDP-glucose synthase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65245.1 cloW	38863 - 39459 (+)	dTDP-4-keto-6-deoxyglucose 3,5-epimerase	Scaffold biosynthesis		copy AA seq copy Nt seq
AAN65246.1 cloZ	39459 - 40220 (+)	Unknown			copy AA seq copy Nt seq
AAN65247.1 gyrBR	40574 - >42291 (+)	clorobiocin-resistant gyrase B	Resistance/immunity	Other in vivo study	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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