1.14.13.180: aklavinone 12-hydroxylase
This is an abbreviated version!
For detailed information about aklavinone 12-hydroxylase, go to the full flat file.
Reaction
Synonyms
aklavinone 12-hydroxylase, DnrF, RdmE
ECTree
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Substrates Products
Substrates Products on EC 1.14.13.180 - aklavinone 12-hydroxylase
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REACTION DIAGRAM
11-deoxy-beta-L-rhodomycinone + NADPH + H+ + O2
beta-rhodomycinone + NADP+ + H2O
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11-deoxy-L-rhodomycinone is a better substrate than aklavinone
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?
aklavinone + NADH + H+ + O2
epsilon-rhodomycinone + NAD+ + H2O
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the enzyme participates in the biosynthesis of daunorubicin, doxorubicin and rhodomycins
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C-glucosyl flavokermesic acid + NADPH + H+ + O2
carminic acid + NADP+ + H2O
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?
flavokermesic acid + NADPH + H+ + O2
kermesic acid + NADP+ + H2O
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additional information
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no activity with decarbomethoxyaklavinone or 15-demethoxyaklavinone
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?
epsilon-rhodomycinone + NADP+ + H2O
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
modifications of the aklavinone molecule can influence the efficiency of the hydroxylation carried out by DnrF. While molecules modified in positions C-10 and C-13 are hydroxylated as efficiently as aklavinone (11-deoxycarminomycinone conversion), molecules 14-hydroxylated or 4-methylated are very poor substrates (11-deoxy-4-demethyladriamycinone and 11-deoxydaunomycinone conversion)
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
modifications of the aklavinone molecule can influence the efficiency of the hydroxylation carried out by DnrF. While molecules modified in positions C-10 and C-13 are hydroxylated as efficiently as aklavinone (11-deoxycarminomycinone conversion), molecules 14-hydroxylated or 4-methylated are very poor substrates (11-deoxy-4-demethyladriamycinone and 11-deoxydaunomycinone conversion)
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
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?
aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
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the enzyme is involved in the biosynthesis of the anthracycline antibiotic daunorubicin/doxorubicin pathway. During the biosynthesis of L-rhodomycins, RdmE first modifies aklavinone at C-11, and epsilon-rhodomycinone or aklavinone is subsequently glycosylated
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aklavinone + NADPH + H+ + O2
epsilon-rhodomycinone + NADP+ + H2O
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about 60% compared to the activity with 11-deoxy-L-rhodomycinone
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?