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13-deoxycarminomycin + NADPH + H+ + O2
13-dihydrocarminomycin + NADP+ + H2O
13-deoxydaunorubicin + NADPH + H+ + O2
13-dihydrodaunorubicin + NADP+ + H2O
13-deoxydaunorubicin + NADPH + H+ + O2
daunorubicinol + NADP+ + H2O
-
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2
carminomycin + NADP+ + H2O
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + 2 H2O
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
daunomycin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
resveratrol + NADPH + H+ + O2
piceatannol + NADP+ + H2O
DoxA along with accessory enzymes ferrdoxin reductase and ferredoxin from spinach hydroxylates resveratrol at the 3'-position in vitro to produce piceatannol
-
-
?
additional information
?
-
13-deoxycarminomycin + NADPH + H+ + O2

13-dihydrocarminomycin + NADP+ + H2O
-
-
-
?
13-deoxycarminomycin + NADPH + H+ + O2
13-dihydrocarminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-deoxycarminomycin + NADPH + H+ + O2
13-dihydrocarminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
13-deoxydaunorubicin + NADPH + H+ + O2

13-dihydrodaunorubicin + NADP+ + H2O
-
i.e. daunorubicinol
-
?
13-deoxydaunorubicin + NADPH + H+ + O2
13-dihydrodaunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-deoxydaunorubicin + NADPH + H+ + O2
13-dihydrodaunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2

carminomycin + NADP+ + H2O
-
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2
carminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2
carminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
13-dihydrodaunorubicin + NADPH + H+ + O2

daunorubicin + NADP+ + 2 H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + 2 H2O
i.e. daunorubicinol
-
-
?
daunomycin + NADPH + H+ + O2

doxorubicin + NADP+ + H2O
-
-
-
?
daunomycin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and 13-dihydrodaunorubicin and the hydroxylation at C-14 of daunorubicin
-
-
?
daunorubicin + NADPH + H+ + O2

doxorubicin + NADP+ + H2O
-
-
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
-
-
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
-
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
additional information

?
-
the enzyme convert daunomycin to doxorubicin
-
-
?
additional information
?
-
daunomycinone (daunomycin aglycone), carminomycin, 13-dihydrocarminomycin, idarubicin, and aklavin are not apparent substrates for DoxA
-
-
?
additional information
?
-
the enzyme shows broad substrate specificity for anthracycline glycone substrates. DoxA has a strong preference for 4-methoxyanthracycline intermediates over their 4-hydroxy analogues as well as a preference for hydroxylation of the C-13 position over the C-14 position
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-
?
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13-deoxycarminomycin + NADPH + H+ + O2
13-dihydrocarminomycin + NADP+ + H2O
13-deoxydaunorubicin + NADPH + H+ + O2
13-dihydrodaunorubicin + NADP+ + H2O
13-dihydrocarminomycin + NADPH + H+ + O2
carminomycin + NADP+ + H2O
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + 2 H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
daunomycin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and 13-dihydrodaunorubicin and the hydroxylation at C-14 of daunorubicin
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
additional information
?
-
the enzyme convert daunomycin to doxorubicin
-
-
?
13-deoxycarminomycin + NADPH + H+ + O2

13-dihydrocarminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-deoxycarminomycin + NADPH + H+ + O2
13-dihydrocarminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
13-deoxydaunorubicin + NADPH + H+ + O2

13-dihydrodaunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-deoxydaunorubicin + NADPH + H+ + O2
13-dihydrodaunorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2

carminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin
-
-
?
13-dihydrocarminomycin + NADPH + H+ + O2
carminomycin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
daunorubicin + NADPH + H+ + O2

doxorubicin + NADP+ + H2O
-
-
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
-
-
-
-
?
daunorubicin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and daunorubicinol and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
-
-
?
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malfunction
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the block in the SPDHC mutant is probably due to a defective C-13 oxidation activity of DoxA. Since this mutant accumulates 13-dihydrocarminomycin, the C-13 hydroxylation activity of DoxA is probably not affected
physiological function

DoxA catalyzes three steps in the daunorubicin/doxorubicin biosynthesis pathway: hydroxylation at C13 of 13-deoxycarminomycin and 13-deoxydaunorubicin, oxidation at C-13 of 13-dihydrocarminomycin and 13-dihydrodaunorubicin and the hydroxylation at C-14 of daunorubicin. It appears that the primary function of DoxA is to catalyze the enzymatic conversion of 13-deoxydaunorubicin to daunorubicin via daunorubicinol
physiological function
-
the cytochrome P450 monoxygenase DoxA is responsible for the hydroxylation of daunorubicin into doxorubicin
physiological function
-
the cytochrome P450 monoxygenase DoxA is responsible for the hydroxylation of daunorubicin into doxorubicin
-
additional information

-
protein-protein interaction and docking analysis of recombinant enzymes, structure homology modeling, DoxA active site structure, overview. Enzyme DoxA interacts with ist redox partners FDX1, FDR2, and FDX3
additional information
-
protein-protein interaction and docking analysis of recombinant enzymes, structure homology modeling, DoxA active site structure, overview. Enzyme DoxA interacts with ist redox partners FDX1, FDR2, and FDX3
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Dickens, M.L.; Strohl, W.R.
Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24
J. Bacteriol.
178
3389-3395
1996
Streptomyces sp. (Q59971)
brenda
Dickens, M.L.; Priestley, N.D.; Strohl, W.R.
In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA
J. Bacteriol.
179
2641-2650
1997
Streptomyces sp. (Q59971)
brenda
Walczak, R.J.; Dickens, M.L.; Priestley, N.D.; Strohl, W.R.
Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis
J. Bacteriol.
181
298-304
1999
Streptomyces sp. (Q59971)
brenda
Lomovskaya, N.; Otten, S.L.; Doi-Katayama, Y.; Fonstein, L.; Liu, X.C.; Takatsu, T.; Inventi-Solari, A.; Filippini, S.; Torti, F.; Colombo, A.L.; Hutchinson, C.R.
Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene
J. Bacteriol.
181
305-318
1999
Streptomyces peucetius (Q9ZAU3), Streptomyces peucetius ATCC 29050 (Q9ZAU3)
brenda
Vetrive,l K.S.; Dharmalingam, K.
Isolation and characterization of stable mutants of Streptomyces peucetius defective in daunorubicin biosynthesis
J. Genet.
80
31-38
2001
Streptomyces peucetius
brenda
Rimal, H.; Lee, S.; Lee, J.; Oh, T.
Understanding of real alternative redox partner of Streptomyces peucetius DoxA Prediction and validation using in silico and in vitro analyses
Arch. Biochem. Biophys.
585
64-74
2015
Streptomyces peucetius, Streptomyces peucetius ATCC 27952
brenda
Rimal, H.; Yu, S.C.; Lee, J.H.; Tokutaro, Y.; Oh, T.J.
Hydroxylation of resveratrol with DoxA in vitro an enzyme with the potential for the bioconversion of a bioactive stilbene
J. Microbiol. Biotechnol.
28
561-565
2018
Streptomyces peucetius (Q9ZAU3)
brenda