1.14.13.181: 13-deoxydaunorubicin hydroxylase
This is an abbreviated version!
For detailed information about 13-deoxydaunorubicin hydroxylase, go to the full flat file.
Reaction
Synonyms
CYP109A2, DoxA, DoxA monooxygenase
ECTree
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Substrates Products
Substrates Products on EC 1.14.13.181 - 13-deoxydaunorubicin hydroxylase
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REACTION DIAGRAM
13-deoxydaunorubicin + NADPH + H+ + O2
daunorubicinol + NADP+ + H2O
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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
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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
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13-dihydrocarminomycin + NADP+ + H2O
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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
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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-dihydrodaunorubicin + NADP+ + H2O
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i.e. daunorubicinol
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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
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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
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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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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
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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
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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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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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