Actinorhodin : Cluster information
Compound
Entry name | Actinorhodin |
---|---|
PKS Type | TypeII |
Starter Unit | malonyl-CoA |
Chain Length | 8 |
Sugar Unit | none |
Classification | Benzoisochromanequinone (BIQ) |
Activity | Antibacterial Organocatalysis |
Composition | C32H26O14 |
Original source
Organism | Streptomyces coelicolor |
---|---|
Strain | A3(2) (=NBRC 15146) |
Contig | X62373 X58833 M64683 M19536 X63449 |
PKS/NRPS Module
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Reference
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- Fernandez-Moreno MA, Martinez E, Boto L, Hopwood DA, Malpartida F[PMID: 1527048]J Biol Chem. 267 (1992) 19278-90
- Transcriptional organization and regulation of an antibiotic export complex in the producing Streptomyces culture.
- Caballero JL, Malpartida F, Hopwood DA[PMID: 1716725]Mol Gen Genet. 228 (1991) 372-80
- Organisation and functions of the actVA region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor.
- Caballero JL, Martinez E, Malpartida F, Hopwood DA[PMID: 1766437]Mol Gen Genet. 230 (1991) 401-12
- The act cluster contains regulatory and antibiotic export genes, direct targets for translational control by the bldA tRNA gene of Streptomyces.
- Fernandez-Moreno MA, Caballero JL, Hopwood DA, Malpartida F[PMID: 1878971]Cell. 66 (1991) 769-80
- Biosynthesis of anthraquinones by interspecies cloning of actinorhodin biosynthesis genes in streptomycetes: clarification of actinorhodin gene functions.
- Bartel PL, Zhu CB, Lampel JS, Dosch DC, Connors NC, Strohl WR, Beale JM Jr, Floss HG[PMID: 2394677]J Bacteriol. 172 (1990) 4816-26
- Nucleotide sequence, transcription and deduced function of a gene involved in polyketide antibiotic synthesis in Streptomyces coelicolor.
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- Identification of a flavin:NADH oxidoreductase involved in the biosynthesis of actinorhodin. Purification and characterization of the recombinant enzyme.
- Kendrew SG, Harding SE, Hopwood DA, Marsh EN[PMID: 7615536]J Biol Chem. 270 (1995) 17339-43
- Stationary-phase production of the antibiotic actinorhodin in Streptomyces coelicolor A3(2) is transcriptionally regulated.
- Gramajo HC, Takano E, Bibb MJ[PMID: 7683365]Mol Microbiol. 7 (1993) 837-45
- DNA sequence and functions of the actVI region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor A3(2).
- Fernandez-Moreno MA, Martinez E, Caballero JL, Ichinose K, Hopwood DA, Malpartida F[PMID: 7929165]J Biol Chem. 269 (1994) 24854-63
- Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2).
- Bystrykh LV, Fernandez-Moreno MA, Herrema JK, Malpartida F, Hopwood DA, Dijkhuizen L[PMID: 8636024]J Bacteriol. 178 (1996) 2238-44
- Identification of a monooxygenase from Streptomyces coelicolor A3(2) involved in biosynthesis of actinorhodin: purification and characterization of the recombinant enzyme.
- Kendrew SG, Hopwood DA, Marsh EN[PMID: 9209048]J Bacteriol. 179 (1997) 4305-10
- Proof that the ACTVI genetic region of Streptomyces coelicolor A3(2) is involved in stereospecific pyran ring formation in the biosynthesis of actinorhodin.
- Ichinose K, Surti C, Taguchi T, Malpartida F, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Hopwood DA[PMID: 10091691]Bioorg Med Chem Lett. 9 (1999) 395-400
- A chain initiation factor common to both modular and aromatic polyketide synthases.
- Bisang C, Long PF, Cortes J, Westcott J, Crosby J, Matharu AL, Cox RJ, Simpson TJ, Staunton J, Leadlay PF[PMID: 10519556]Nature. 401 (1999) 502-5
- Mechanistic analysis of a type II polyketide synthase. Role of conserved residues in the beta-ketoacyl synthase-chain length factor heterodimer.
- Dreier J, Khosla C[PMID: 10684659]Biochemistry. 39 (2000) 2088-95
- Chemical characterisation of disruptants of the Streptomyces coelicolor A3(2) actVI genes involved in actinorhodin biosynthesis.
- Taguchi T, Itou K, Ebizuka Y, Malpartida F, Hopwood DA, Surti CM, Booker-Milburn KI, Stephenson GR, Ichinose K[PMID: 10805574]J Antibiot (Tokyo). 53 (2000) 144-52
- Genetic Contributions to Understanding Polyketide Synthases.
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- Primary and secondary metabolism, and post-translational protein modifications, as portrayed by proteomic analysis of Streptomyces coelicolor.
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- An antibiotic factory caught in action.
- Keatinge-Clay AT, Maltby DA, Medzihradszky KF, Khosla C, Stroud RM[PMID: 15286722]Nat Struct Mol Biol. 11 (2004) 888-93
- The crystal structure of the actIII actinorhodin polyketide reductase: proposed mechanism for ACP and polyketide binding.
- Hadfield AT, Limpkin C, Teartasin W, Simpson TJ, Crosby J, Crump MP[PMID: 15458634]Structure. 12 (2004) 1865-75
- Remarkably different structures and reaction mechanisms of ketoreductases for the opposite stereochemical control in the biosynthesis of BIQ antibiotics.
- Taguchi T, Kunieda K, Takeda-Shitaka M, Takaya D, Kawano N, Kimberley MR, Booker-Milburn KI, Stephenson GR, Umeyama H, Ebizuka Y, Ichinose K[PMID: 15498668]Bioorg Med Chem. 12 (2004) 5917-27
- Transcriptional activation of the pathway-specific regulator of the actinorhodin biosynthetic genes in Streptomyces coelicolor.
- Uguru GC, Stephens KE, Stead JA, Towle JE, Baumberg S, McDowall KJ[PMID: 16164554]Mol Microbiol. 58 (2005) 131-50
- Self-malonylation is an intrinsic property of a chemically synthesized type II polyketide synthase acyl carrier protein.
- Arthur CJ, Szafranska A, Evans SE, Findlow SC, Burston SG, Owen P, Clark-Lewis I, Simpson TJ, Crosby J, Crump MP[PMID: 16285746]Biochemistry. 44 (2005) 15414-21
- Possible involvement of ActVI-ORFA in transcriptional regulation of actVI tailoring-step genes for actinorhodin biosynthesis.
- Taguchi T, Okamoto S, Lezhava A, Li A, Ochi K, Ebizuka Y, Ichinose K[PMID: 17227452]FEMS Microbiol Lett. 269 (2007) 234-9
- Initiation of actinorhodin export in Streptomyces coelicolor.
- Tahlan K, Ahn SK, Sing A, Bodnaruk TD, Willems AR, Davidson AR, Nodwell JR[PMID: 17338074]Mol Microbiol. 63 (2007) 951-61
- Actinorhodin biosynthesis: structural requirements for post-PKS tailoring intermediates revealed by functional analysis of ActVI-ORF1 reductase.
- Itoh T, Taguchi T, Kimberley MR, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Ichinose K[PMID: 17579485]Biochemistry. 46 (2007) 8181-8
- Investigation of transcription repression and small-molecule responsiveness by TetR-like transcription factors using a heterologous Escherichia coli-based assay.
- Ahn SK, Tahlan K, Yu Z, Nodwell J[PMID: 17644591]J Bacteriol. 189 (2007) 6655-64
- Dissecting the component reactions catalyzed by the actinorhodin minimal polyketide synthase.
- Beltran-Alvarez P, Cox RJ, Crosby J, Simpson TJ[PMID: 18034463]Biochemistry. 46 (2007) 14672-81
- Inhibition kinetics and emodin cocrystal structure of a type II polyketide ketoreductase.
- Korman TP, Tan YH, Wong J, Luo R, Tsai SC[PMID: 18205400]Biochemistry. 47 (2008) 1837-47
- Crystal structures of the Streptomyces coelicolor TetR-like protein ActR alone and in complex with actinorhodin or the actinorhodin biosynthetic precursor (S)-DNPA.
- Willems AR, Tahlan K, Taguchi T, Zhang K, Lee ZZ, Ichinose K, Junop MS, Nodwell JR[PMID: 18207163]J Mol Biol. 376 (2008) 1377-87
- Mechanism and regulation of the Two-component FMN-dependent monooxygenase ActVA-ActVB from Streptomyces coelicolor.
- Valton J, Mathevon C, Fontecave M, Niviere V, Ballou DP[PMID: 18245777]J Biol Chem. 283 (2008) 10287-96
- Localization of the ActIII actinorhodin polyketide ketoreductase to the cell wall.
- Xu XP, Wang ZJ, Fan KQ, Wang SL, Jia CJ, Han H, Ramalingam E, Yang KQ[PMID: 18691223]FEMS Microbiol Lett. 287 (2008) 15-21
- Ligand recognition by ActR, a TetR-like regulator of actinorhodin export.
- Tahlan K, Yu Z, Xu Y, Davidson AR, Nodwell JR[PMID: 18804114]J Mol Biol. 383 (2008) 753-61
- Biosynthesis of actinorhodin and related antibiotics: discovery of alternative routes for quinone formation encoded in the act gene cluster.
- Okamoto S, Taguchi T, Ochi K, Ichinose K[PMID: 19246012]Chem Biol. 16 (2009) 226-36
- Biosynthesis of aromatic polyketides in bacteria.
- Das A, Khosla C[PMID: 19292437]Acc Chem Res. 42 (2009) 631-9
- Probing the Interactions of early polyketide intermediates with the Actinorhodin ACP from S. coelicolor A3(2).
- Evans SE, Williams C, Arthur CJ, Ploskon E, Wattana-amorn P, Cox RJ, Crosby J, Willis CL, Simpson TJ, Crump MP[PMID: 19361520]J Mol Biol. 389 (2009) 511-28
- Preliminary kinetic analysis of acyl carrier protein-ketoacylsynthase interactions in the actinorhodin minimal polyketide synthase.
- Beltran-Alvarez P, Arthur CJ, Cox RJ, Crosby J, Crump MP, Simpson TJ[PMID: 19381365]Mol Biosyst. 5 (2009) 511-8
- Structural and biochemical analyses of regio- and stereospecificities observed in a type II polyketide ketoreductase.
- Javidpour P, Korman TP, Shakya G, Tsai SC[PMID: 21506596]Biochemistry. 50 (2011) 4638-49
- Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin.
- Taguchi T, Okamoto S, Hasegawa K, Ichinose K[PMID: 22086671]Chembiochem. 12 (2011) 2767-73
- Identification of the actinorhodin monomer and its related compound from a deletion mutant of the actVA-ORF4 gene of Streptomyces coelicolor A3(2).
- Taguchi T, Ebihara T, Furukawa A, Hidaka Y, Ariga R, Okamoto S, Ichinose K[PMID: 22765902]Bioorg Med Chem Lett. (2012)
- A two-step mechanism for the activation of actinorhodin export and resistance in Streptomyces coelicolor.
- Xu Y, Willems A, Au-Yeung C, Tahlan K, Nodwell JR[PMID: 23073761]MBio. 3 (2012) e00191-12
- Biosynthetic conclusions from the functional dissection of oxygenases for biosynthesis of actinorhodin and related streptomyces antibiotics.
- Taguchi T, Yabe M, Odaki H, Shinozaki M, Metsa-Ketela M, Arai T, Okamoto S, Ichinose K[PMID: 23601640]Chem Biol. 20 (2013) 510-20
- The determinants of activity and specificity in actinorhodin type II polyketide ketoreductase.
- Javidpour P, Bruegger J, Srithahan S, Korman TP, Crump MP, Crosby J, Burkart MD, Tsai SC[PMID: 24035284]Chem Biol. 20 (2013) 1225-34
- Modeling linear and cyclic PKS intermediates through atom replacement.
- Shakya G, Rivera H Jr, Lee DJ, Jaremko MJ, La Clair JJ, Fox DT, Haushalter RW, Schaub AJ, Bruegger J, Barajas JF, White AR, Kaur P, Gwozdziowski ER, Wong F, Tsai SC, Burkart MD[PMID: 25406716]J Am Chem Soc. 136 (2014) 16792-9
- Structure and biosynthetic implication of 5R-(N-acetyl-L-cysteinyl)-14S-hydroxy-dihydrokalafungin from a mutant of the actVA-ORF4 gene for actinorhodin biosynthesis in Streptomyces coelicolor A3(2).
- Taguchi T, Maruyama T, Sawa R, Igarashi M, Okamoto S, Ichinose K[PMID: 25690356]J Antibiot (Tokyo). 68 (2015) 481-3
- Highly efficient editing of the actinorhodin polyketide chain length factor gene in Streptomyces coelicolor M145 using CRISPR/Cas9-CodA(sm) combined system.
- Zeng H, Wen S, Xu W, He Z, Zhai G, Liu Y, Deng Z, Sun Y[PMID: 26318449]Appl Microbiol Biotechnol. 99 (2015) 10575-85
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History
- 2016-12-27[Update]
- 2016-01-27[Update]
- 2013-12-27[Update]
- 2013-05-28[Update]
- 2013-01-16[Update]
- 2012-10-02[Update]
- 2012-08-03[Update]
- 2012-06-04[Release]