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Cluster information : Doxorubicin


close this sectionCompound

Entry nameDoxorubicin
PKS TypeTypeII
Starter Unitpropionyl-CoA
Chain Length10
Sugar UnitL-daunosamine
ClassificationAnthracycline
ActivityAntitumor
CompositionC27H29NO11
Doxorubicin

close this sectionOriginal source


close this sectionPKS/NRPS Module

KS113..339
KS3..375
CLF26..382
ACP5..77

close this sectionReference

Regulation of secondary metabolism in Streptomyces spp. and overproduction of daunorubicin in Streptomyces peucetius.
Stutzman-Engwall KJ, Otten SL, Hutchinson CR
[PMID: 1729206]J Bacteriol. 174 (1992) 144-54
A bacterial analog of the mdr gene of mammalian tumor cells is present in Streptomyces peucetius, the producer of daunorubicin and doxorubicin.
Guilfoile PG, Hutchinson CR
[PMID: 1924314]Proc Natl Acad Sci U S A. 88 (1991) 8553-7
Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis.
Otten SL, Liu X, Ferguson J, Hutchinson CR
[PMID: 7592454]J Bacteriol. 177 (1995) 6688-92
Functional characterization and transcriptional analysis of a gene cluster governing early and late steps in daunorubicin biosynthesis in Streptomyces peucetius.
Madduri K, Hutchinson CR
[PMID: 7601857]J Bacteriol. 177 (1995) 3879-84
Streptomyces peucetius daunorubicin biosynthesis gene, dnrF: sequence and heterologous expression.
Filippini S, Solinas MM, Breme U, Schluter MB, Gabellini D, Biamonti G, Colombo AL, Garofano L
[PMID: 7773378]Microbiology. 141 ( Pt 4) (1995) 1007-16
Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase.
Grimm A, Madduri K, Ali A, Hutchinson CR
[PMID: 7828855]Gene. 151 (1994) 1-10
Functional characterization and transcriptional analysis of the dnrR1 locus, which controls daunorubicin biosynthesis in Streptomyces peucetius.
Madduri K, Hutchinson CR
[PMID: 7868593]J Bacteriol. 177 (1995) 1208-15
Regulation of daunorubicin production in Streptomyces peucetius by the dnrR2 locus.
Otten SL, Ferguson J, Hutchinson CR
[PMID: 7868594]J Bacteriol. 177 (1995) 1216-24
Cloning and sequencing of a gene encoding carminomycin 4-O-methyltransferase from Streptomyces peucetius and its expression in Escherichia coli.
Madduri K, Torti F, Colombo AL, Hutchinson CR
[PMID: 8509343]J Bacteriol. 175 (1993) 3900-4
The Streptomyces peucetius drrC gene encodes a UvrA-like protein involved in daunorubicin resistance and production.
Lomovskaya N, Hong SK, Kim SU, Fonstein L, Furuya K, Hutchinson RC
[PMID: 8655504]J Bacteriol. 178 (1996) 3238-45
The DnrN protein of Streptomyces peucetius, a pseudo-response regulator, is a DNA-binding protein involved in the regulation of daunorubicin biosynthesis.
Furuya K, Hutchinson CR
[PMID: 8892835]J Bacteriol. 178 (1996) 6310-8
The dnrM gene in Streptomyces peucetius contains a naturally occurring frameshift mutation that is suppressed by another locus outside of the daunorubicin-production gene cluster.
Gallo MA, Ward J, Hutchinson CR
[PMID: 8932700]Microbiology. 142 ( Pt 2) (1996) 269-75
Enhanced antibiotic production by manipulation of the Streptomyces peucetius dnrH and dnmT genes involved in doxorubicin (adriamycin) biosynthesis.
Scotti C, Hutchinson CR
[PMID: 8955419]J Bacteriol. 178 (1996) 7316-21
Purification and characterization of the DNA-binding protein DnrI, a transcriptional factor of daunorubicin biosynthesis in Streptomyces peucetius.
Tang L, Grimm A, Zhang YX, Hutchinson CR
[PMID: 8971703]Mol Microbiol. 22 (1996) 801-13
Expression and characterization of DrrA and DrrB proteins of Streptomyces peucetius in Escherichia coli: DrrA is an ATP binding protein.
Kaur P
[PMID: 9006006]J Bacteriol. 179 (1997) 569-75
Cloning and characterization of the Streptomyces peucetius dnmZUV genes encoding three enzymes required for biosynthesis of the daunorubicin precursor thymidine diphospho-L-daunosamine.
Otten SL, Gallo MA, Madduri K, Liu X, Hutchinson CR
[PMID: 9209071]J Bacteriol. 179 (1997) 4446-50
Iterative type II polyketide synthases, cyclases and ketoreductases exhibit context-dependent behavior in the biosynthesis of linear and angular decapolyketides.
Meurer G, Gerlitz M, Wendt-Pienkowski E, Vining LC, Rohr J, Hutchinson CR
[PMID: 9224566]Chem Biol. 4 (1997) 433-43
Production of the antitumor drug epirubicin (4'-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius.
Madduri K, Kennedy J, Rivola G, Inventi-Solari A, Filippini S, Zanuso G, Colombo AL, Gewain KM, Occi JL, MacNeil DJ, Hutchinson CR
[PMID: 9447597]Nat Biotechnol. 16 (1998) 69-74
The Streptomyces peucetius dpsY and dnrX genes govern early and late steps of daunorubicin and doxorubicin biosynthesis.
Lomovskaya N, Doi-Katayama Y, Filippini S, Nastro C, Fonstein L, Gallo M, Colombo AL, Hutchinson CR
[PMID: 9573189]J Bacteriol. 180 (1998) 2379-86
The DrrC protein of Streptomyces peucetius, a UvrA-like protein, is a DNA-binding protein whose gene is induced by daunorubicin.
Furuya K, Hutchinson CR
[PMID: 9835035]FEMS Microbiol Lett. 168 (1998) 243-9
Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene.
Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR
[PMID: 9864344]J Bacteriol. 181 (1999) 305-18
DnrD cyclase involved in the biosynthesis of doxorubicin: purification and characterization of the recombinant enzyme.
Kendrew SG, Katayama K, Deutsch E, Madduri K, Hutchinson CR
[PMID: 10200167]Biochemistry. 38 (1999) 4794-9
The Streptomyces peucetius dpsC gene determines the choice of starter unit in biosynthesis of the daunorubicin polyketide.
Bao W, Sheldon PJ, Wendt-Pienkowski E, Hutchinson CR
[PMID: 10419974]J Bacteriol. 181 (1999) 4690-5
Purification and properties of the Streptomyces peucetius DpsC beta-ketoacyl:acyl carrier protein synthase III that specifies the propionate-starter unit for type II polyketide biosynthesis.
Bao W, Sheldon PJ, Hutchinson CR
[PMID: 10423255]Biochemistry. 38 (1999) 9752-7
A two-plasmid system for the glycosylation of polyketide antibiotics: bioconversion of epsilon-rhodomycinone to rhodomycin D.
Olano C, Lomovskaya N, Fonstein L, Roll JT, Hutchinson CR
[PMID: 10631513]Chem Biol. 6 (1999) 845-55
The dnrO gene encodes a DNA-binding protein that regulates daunorubicin production in Streptomyces peucetius by controlling expression of the dnrN pseudo response regulator gene.
Otten SL, Olano C, Hutchinson CR
[PMID: 10846224]Microbiology. 146 ( Pt 6) (2000) 1457-68
Analysis of genes involved in 6-deoxyhexose biosynthesis and transfer in Saccharopolyspora erythraea.
Doumith M, Weingarten P, Wehmeier UF, Salah-Bey K, Benhamou B, Capdevila C, Michel JM, Piepersberg W, Raynal MC
[PMID: 11129052]Mol Gen Genet. 264 (2000) 477-85
Production of aromatic minimal polyketides by the daunorubicin polyketide synthase genes reveals the incompatibility of the heterologous DpsY and JadI cyclases.
Wohlert SE, Wendt-Pienkowski E, Bao W, Hutchinson CR
[PMID: 11520231]J Nat Prod. 64 (2001) 1077-80
Studies on a second and third ring cyclization in anthracycline biosynthesis.
Hautala A, Torkkell S, Raty K, Kunnari T, Kantola J, Mantsala P, Hakala J, Ylihonko K
[PMID: 12715874]J Antibiot (Tokyo). 56 (2003) 143-53
Crystal structure of a ternary complex of DnrK, a methyltransferase in daunorubicin biosynthesis, with bound products.
Jansson A, Koskiniemi H, Mantsala P, Niemi J, Schneider G
[PMID: 15273252]J Biol Chem. 279 (2004) 41149-56
Biochemical characterization of domains in the membrane subunit DrrB that interact with the ABC subunit DrrA: identification of a conserved motif.
Kaur P, Rao DK, Gandlur SM
[PMID: 15709779]Biochemistry. 44 (2005) 2661-70
Feedback regulation of doxorubicin biosynthesis in Streptomyces peucetius.
Jiang H, Hutchinson CR
[PMID: 16545946]Res Microbiol. 157 (2006) 666-74
Functional analysis of desVIII homologues involved in glycosylation of macrolide antibiotics by interspecies complementation.
Hong JS, Park SJ, Parajuli N, Park SR, Koh HS, Jung WS, Choi CY, Yoon YJ
[PMID: 17049185]Gene. 386 (2007) 123-30
Translational coupling controls expression and function of the DrrAB drug efflux pump.
Pradhan P, Li W, Kaur P
[PMID: 19063901]J Mol Biol. 385 (2009) 831-42
The activator/repressor protein DnrO of Streptomyces peucetius binds to DNA without changing its topology.
Ajithkumar V, Prasad R
[PMID: 20122958]Int J Biol Macromol. 46 (2010) 380-4
Daunorubicin efflux in Streptomyces peucetius modulates biosynthesis by feedback regulation.
Srinivasan P, Palani SN, Prasad R
[PMID: 20158521]FEMS Microbiol Lett. 305 (2010) 18-27
Modulation of dnrN expression by intracellular levels of DnrO and daunorubicin in Streptomyces peucetius.
Ajithkumar V, Prasad R
[PMID: 20529134]FEMS Microbiol Lett. 306 (2010) 160-7
Nitrososynthase-triggered oxidative carbon-carbon bond cleavage in baumycin biosynthesis.
Al-Mestarihi A, Romo A, Liu HW, Bachmann BO
[PMID: 23885759]J Am Chem Soc. 135 (2013) 11457-60
The DrrAB efflux system of Streptomyces peucetius is a multidrug transporter of broad substrate specificity.
Li W, Sharma M, Kaur P
[PMID: 24634217]J Biol Chem. 289 (2014) 12633-46
Characterization of a novel domain 'GATE' in the ABC protein DrrA and its role in drug efflux by the DrrAB complex.
Zhang H, Rahman S, Li W, Fu G, Kaur P
[PMID: 25721665]Biochem Biophys Res Commun. 459 (2015) 148-53
Structure of DnmZ, a nitrososynthase in the Streptomyces peucetius anthracycline biosynthetic pathway.
Sartor L, Ibarra C, Al-Mestarihi A, Bachmann BO, Vey JL
[PMID: 26457508]Acta Crystallogr F Struct Biol Commun. 71 (2015) 1205-14

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Doxorubicin
Genomic nucleotide sequence
43 KB
Nucleotide sequences of the coding regions
12 KB
Translation of the coding sequences
9 KB
List of genes/ORFs
2 KB

 

 
GenBank format
89 KB
L47163
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
1 KB
Translation of the coding sequences
599 B
List of genes/ORFs
501 B

 

 

 
L37338
Genomic nucleotide sequence
2 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
706 B
List of genes/ORFs
430 B

 

 

 
U18082
Genomic nucleotide sequence
2 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
579 B
List of genes/ORFs
283 B

 

 

 
M73758
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
1014 B
List of genes/ORFs
558 B

 

 

 
AF048833
Genomic nucleotide sequence
2 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
847 B
List of genes/ORFs
413 B

 

 

 
AF006633
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
3 KB
Translation of the coding sequences
1 KB
List of genes/ORFs
633 B

 

 

 
M80237
Genomic nucleotide sequence
2 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
761 B
List of genes/ORFs
398 B

 

 

 
U77891
Genomic nucleotide sequence
7 KB
Nucleotide sequences of the coding regions
7 KB
Translation of the coding sequences
3 KB
List of genes/ORFs
1 KB

 

 

 
L35560
Genomic nucleotide sequence
9 KB
Nucleotide sequences of the coding regions
9 KB
Translation of the coding sequences
4 KB
List of genes/ORFs
1 KB

 

 

 
L40425
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
3 KB
Translation of the coding sequences
1 KB
List of genes/ORFs
581 B

 

 

 
L47164
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
3 KB
Translation of the coding sequences
1 KB
List of genes/ORFs
425 B

 

 

 
L76359
Genomic nucleotide sequence
3 KB
Nucleotide sequences of the coding regions
2 KB
Translation of the coding sequences
856 B
List of genes/ORFs
261 B

 

 

 

close this sectionHistory

  • 2016-12-27[Update]
  • 2016-01-27[Update]
  • 2014-06-25[Update]
  • 2013-01-16[Update]
  • 2012-10-02[Release]