Aureothin : Cluster information

Compound

Entry name	Aureothin
PKS Type	TypeI iterative
Starter Unit	p-nitrobenzoate
Chain Length	6
Sugar Unit	none
Classification
Activity	Antitumor Antifungal Insecticidal
Composition	C₂₂H₂₃NO₆

Original source

Organism	Streptomyces thioluteus
Strain	HKI-227
Contig	AJ575648

PKS/NRPS Module

Aureo_00040 aurA	0
Aureo_00040 aurA	1	methylmalonyl-CoA
Aureo_00070 aurB	2	malonyl-CoA
Aureo_00080 aurC	3	methylmalonyl-CoA
Aureo_00080 aurC	4

ACP	19..96

KS	116..490

AT	648..966

DH	1015..1177

KR	1497..1676

ACP	1783..1853

KS	34..409

AT	564..884

DH	932..1096

ER	1414..1719

KR	1729..1910

ACP	2012..2082

KS	34..408

AT	572..892

ACP	964..1034

KS	1056..1434

at	1598..1694

ACP	1843..1913

TE	1987..2197

Reference

Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster.: He J, Hertweck C
[PMID: 14700630]Chem Biol. 10 (2003) 1225-32
Biosynthetic origin of the rare nitroaryl moiety of the polyketide antibiotic aureothin: involvement of an unprecedented N-oxygenase.: He J, Hertweck C
[PMID: 15038705]J Am Chem Soc. 126 (2004) 3694-5
Formation of the aureothin tetrahydrofuran ring by a bifunctional cytochrome p450 monooxygenase.: He J, Muller M, Hertweck C
[PMID: 15612710]J Am Chem Soc. 126 (2004) 16742-3
Functional analysis of the aureothin iterative type I polyketide synthase.: He J, Hertweck C
[PMID: 15812854]Chembiochem. 6 (2005) 908-12
Dissection of the late steps in aureothin biosynthesis.: Muller M, He J, Hertweck C
[PMID: 16292785]Chembiochem. 7 (2006) 37-9
In vitro reconstitution and crystal structure of p-aminobenzoate N-oxygenase (AurF) involved in aureothin biosynthesis.: Choi YS, Zhang H, Brunzelle JS, Nair SK, Zhao H
[PMID: 18458342]Proc Natl Acad Sci U S A. 105 (2008) 6858-63
Chemoenzymatic total synthesis of the antiproliferative polyketide (+)-(R)-aureothin.: Werneburg M, Hertweck C
[PMID: 18690656]Chembiochem. 9 (2008) 2064-6
Sequential asymmetric polyketide heterocyclization catalyzed by a single cytochrome P450 monooxygenase (AurH).: Richter ME, Traitcheva N, Knupfer U, Hertweck C
[PMID: 18855960]Angew Chem Int Ed Engl. 47 (2008) 8872-5
Four-electron oxidation of p-hydroxylaminobenzoate to p-nitrobenzoate by a peroxodiferric complex in AurF from Streptomyces thioluteus.: Li N, Korboukh VK, Krebs C, Bollinger JM Jr
[PMID: 20798054]Proc Natl Acad Sci U S A. 107 (2010) 15722-7
Structural fine-tuning of a multifunctional cytochrome P450 monooxygenase.: Zocher G, Richter ME, Mueller U, Hertweck C
[PMID: 21280577]J Am Chem Soc. 133 (2011) 2292-302
A ribonucleotide reductase-like electron transfer system in the nitroaryl-forming N-oxygenase AurF.: Fries A, Bretschneider T, Winkler R, Hertweck C
[PMID: 21678538]Chembiochem. 12 (2011) 1832-5
Interchenar retrotransfer of aureothin intermediates in an iterative polyketide synthase module.: Busch B, Ueberschaar N, Sugimoto Y, Hertweck C
[PMID: 22799266]J Am Chem Soc. 134 (2012) 12382-5
Multifactorial control of iteration events in a modular polyketide assembly line.: Busch B, Ueberschaar N, Behnken S, Sugimoto Y, Werneburg M, Traitcheva N, He J, Hertweck C
[PMID: 23606628]Angew Chem Int Ed Engl. 52 (2013) 5285-9
Characterization of the N-oxygenase AurF from Streptomyces thioletus.: Chanco E, Choi YS, Sun N, Vu M, Zhao H
[PMID: 24973817]Bioorg Med Chem. 22 (2014) 5569-77
Computational Examination on the Active Site Structure of a (Peroxo)diiron(III) Intermediate in the Amine Oxygenase AurF.: Jayapal P, Ansari A, Rajaraman G
[PMID: 26588098]Inorg Chem. 54 (2015) 11077-82