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The taxonomic range for the selected organisms is: Streptomyces sp.
The enzyme appears in selected viruses and cellular organisms
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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
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-
-
?
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
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
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-
?
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
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-
?
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
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-
-
?
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
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-
?
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
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-
?
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
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-
?
13-dihydrodaunorubicin + NADPH + H+ + O2
daunorubicin + NADP+ + 2 H2O
i.e. daunorubicinol
-
-
?
daunomycin + NADPH + H+ + O2
doxorubicin + NADP+ + H2O
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-
-
?
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
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-
-
?
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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-
?
additional information
?
-
the enzyme convert daunomycin to doxorubicin
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-
?
additional information
?
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daunomycinone (daunomycin aglycone), carminomycin, 13-dihydrocarminomycin, idarubicin, and aklavin are not apparent substrates for DoxA
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-
?
additional information
?
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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
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-
?
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
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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-
?
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
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-
?
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
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-
?
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
-
-
?
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dithiothreitol
strongly inhibitory, inhibition is reversible after desalting
doxorubicin
completely inhibits DoxA activity at both 1 and 5 mM, competitive with respect to daunorubicinol oxidation
quinidine
inhibits DoxA oxidation of daunorubicinol by 11% at 1 mM. At 5 mM, it inhibits at more than 95%
sulfaphenazole
inhibits DoxA oxidation of daunorubicinol by 20% at 1 mM. At 5 mM, it inhibits at more than 95%
troleandomycin
inhibits DoxA oxidation of daunorubicinol by 35% at 1 mM. At 5 mM, it inhibits at more than 95%
additional information
high ionic strength buffers containing 100 mM sodium phosphate, also strongly inhibits DoxA activity. This effect is partially reversible after exchange into low ionic strength buffers, such as 20 mM N-(2-hydroxyethyl)piperazine-N9-(2-ethanesulfonic acid) (HEPES) or 10 mM sodium phosphate (pH 7.5). No inhibition: 4-methylpyrazole (1 or 5 mM), rhodomycin D (1-5 mM)
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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