BGC0000024

BGC0000024: aureothin biosynthetic gene cluster from Streptomyces thioluteus

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Location: 1 - 29,132 nt. (total: 29,132 nt).
This entry is originally from NCBI GenBank AJ575648.1.

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core biosynthetic genes

additional biosynthetic genes

transport-related genes

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Gene details

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General

Compounds

Genes

Biosynthesis

History

NRPS/PKS domains

KnownClusterBlast

General information about the BGC

MIBiG accession	BGC0000024
Short description	aureothin biosynthetic gene cluster from Streptomyces thioluteus
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)	PKS (Type I)
Loci	AJ575648.1 via Knock-out studies, Enzymatic assays, Heterologous expression
Compounds	aureothin
Species	Streptomyces thioluteus [taxonomy]
References	[1] Gamma-pyrone compounds with selective and potent anti-Helicobacter pylori activity. Taniguchi M et al., J Antibiot (Tokyo) (2000) PMID:11079808 [2] Chemical studies on a toxic product of Streptomyces thioluteus, aureothin. WASHIZU F et al., J Antibiot (Tokyo) (1954) PMID:13174453 [3] Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster. He J et al., Chem Biol (2003) PMID:14700630 [4] Biosynthetic origin of the rare nitroaryl moiety of the polyketide antibiotic aureothin: involvement of an unprecedented N-oxygenase. He J et al., J Am Chem Soc (2004) PMID:15038705 [5] Formation of the aureothin tetrahydrofuran ring by a bifunctional cytochrome p450 monooxygenase. He J et al., J Am Chem Soc (2004) PMID:15612710 [6] Mutasynthesis of aureonitrile: an aureothin derivative with significantly improved cytostatic effect. Ziehl M et al., Angew Chem Int Ed Engl (2005) PMID:15645471 [7] Functional analysis of the aureothin iterative type I polyketide synthase. He J et al., Chembiochem (2005) PMID:15812854 [8] Dissection of the late steps in aureothin biosynthesis. Müller M et al., Chembiochem (2006) PMID:16292785 [9] AurF from Streptomyces thioluteus and a possible new family of manganese/iron oxygenases. Krebs C et al., Biochemistry (2007) PMID:17718517 [10] Non-colinear polyketide biosynthesis in the aureothin and neoaureothin pathways: an evolutionary perspective. Traitcheva N et al., Chembiochem (2007) PMID:17763486 [11] Structure and action of the N-oxygenase AurF from Streptomyces thioluteus. Zocher G et al., J Mol Biol (2007) PMID:17765264 [12] In vitro reconstitution and crystal structure of p-aminobenzoate N-oxygenase (AurF) involved in aureothin biosynthesis. Choi YS et al., Proc Natl Acad Sci U S A (2008) PMID:18458342 [13] Exploiting enzymatic promiscuity to engineer a focused library of highly selective antifungal and antiproliferative aureothin analogues. Werneburg M et al., J Am Chem Soc (2010) PMID:20662518 [14] Four-electron oxidation of p-hydroxylaminobenzoate to p-nitrobenzoate by a peroxodiferric complex in AurF from Streptomyces thioluteus. Li N et al., Proc Natl Acad Sci U S A (2010) PMID:20798054 [15] Structural fine-tuning of a multifunctional cytochrome P450 monooxygenase. Zocher G et al., J Am Chem Soc (2011) PMID:21280577 [16] A ribonucleotide reductase-like electron transfer system in the nitroaryl-forming N-oxygenase AurF. Fries A et al., Chembiochem (2011) PMID:21678538 [17] Interchenar retrotransfer of aureothin intermediates in an iterative polyketide synthase module. Busch B et al., J Am Chem Soc (2012) PMID:22799266 [18] Multifactorial control of iteration events in a modular polyketide assembly line. Busch B et al., Angew Chem Int Ed Engl (2013) PMID:23606628 [19] Rational design of modular polyketide synthases: morphing the aureothin pathway into a luteoreticulin assembly line. Sugimoto Y et al., Angew Chem Int Ed Engl (2014) PMID:24402879 [20] Characterization of the N-oxygenase AurF from Streptomyces thioletus. Chanco E et al., Bioorg Med Chem (2014) PMID:24973817 [21] Identification of mycolutein and pulvomycin as aureothin and labilomycin respectively. Schwartz JL et al., J Antibiot (Tokyo) (1976) PMID:770405

Chemical products information

aureothin Evidence:

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C₂₂H₂₃N₁O₆

Chemical database entries
PubCHEM
ChemSpider

List of genes involved in compound(s) production

Identifiers	Position	Product	Functions	Evidence	Extra
CAE02599.1 aurD	2154 - 2969 (+)	AurD protein			copy AA seq copy Nt seq
CAE02600.1 aurE	3029 - 4546 (-)	p-nitrobenzoate CoA ligase	Precursor biosynthesis	Knock-out Other in vivo study	copy AA seq copy Nt seq
CAE02601.1 aurF	4858 - 5868 (+)	p-aminobenzoate N-oxygenase	Precursor biosynthesis	Knock-out Heterologous expression Other in vivo study Activity assay	copy AA seq copy Nt seq
CAE02602.1 aurA	5990 - 11710 (+)	polyketide synthase type I			copy AA seq copy Nt seq
CAE02603.1 aurG	11745 - 13832 (+)	PABA synthase			copy AA seq copy Nt seq
CAE02604.1 aurH	13938 - 15158 (+)	bifunctional cytochrome P450 monooxygenase	Tailoring	Knock-out Heterologous expression Other in vivo study Activity assay	copy AA seq copy Nt seq
CAE02605.1 aurB	15244 - 21738 (+)	polyketide synthase type I			copy AA seq copy Nt seq
CAE02606.1 aurC	21801 - 28406 (+)	polyketide synthase type I			copy AA seq copy Nt seq
CAE02607.1 aurI	28440 - 29132 (+)	O-methyl transferase	Tailoring	Knock-out Other in vivo study	copy AA seq copy Nt seq

Biosynthesis information

Biosynthetic modules

Name

Type

pks-modular

Genes

aurA

Substrates

Integrated Monomers

Domains

acyltransferase, ketosynthase, acyltransferase, ketoreductase, dehydratase, carrier (ACP)

Name

Type

pks-modular

Genes

aurB

Substrates

Integrated Monomers

Domains

acyltransferase, ketosynthase, acyltransferase, ketoreductase, dehydratase, enoylreductase, carrier (ACP)

Name

Type

pks-modular

Genes

aurC

Substrates

Integrated Monomers

Domains

acyltransferase, ketosynthase, acyltransferase, carrier (ACP)

Name

Type

pks-trans-at

Genes

aurC

Substrates

Integrated Monomers

Domains

ketosynthase, carrier (ACP)

Annotation changelog

Entry version: 4

Date

Changes

Submitters

Reviewers

2022-10-07

Update chemical activity to schema version 2.11

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

Entry version: 3

Date

Changes

Submitters

Reviewers

2022-09-15

Removed ketoreductase stereochemistry annotation from modules without ketoreductases

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

2022-09-15

Updated bioactivity data

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

Entry version: 2

Date

Changes

Submitters

Reviewers

2019-10-16

Migrated from v1.4

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

Entry version: 1

Date

Changes

Submitters

Reviewers

2015-06-12

Submitted

(ID: F65XGYSSLMUEJC2Q4T3BLCPS)

(ID: AAAAAAAAAAAAAAAAAAAAAAAA)

Detailed domain annotation

Selected features only

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