Information on EC 1.14.13.37 - methyltetrahydroprotoberberine 14-monooxygenase
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The enzyme appears in viruses and cellular organisms
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methyltetrahydroprotoberberine 14-monooxygenase
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(S)-N-methylcanadine + NADPH + H+ + O2 = allocryptopine + NADP+ + H2O
(S)-N-methylcanadine + NADPH + H+ + O2 = allocryptopine + NADP+ + H2O

stereo- and regiospecificity
Corydalis vaginans
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(S)-N-methylcanadine + NADPH + H+ + O2 = allocryptopine + NADP+ + H2O
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Biosynthesis of secondary metabolites
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chelerythrine biosynthesis
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Isoquinoline alkaloid biosynthesis
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(S)-N-methylcanadine,NADPH:oxygen oxidoreductase (14-hydroxylating)
A heme-thiolate protein (P-450).
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(S)-cis-N-methyltetrahydroprotoberberine-14-hydroxylase
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methyltetrahydroprotoberberine 14-hydroxylase
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oxygenase, (S)-cis-N-methyltetrahydroberberine 14-mono-
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Corydalis vaginans
papaveraceae
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brenda
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(S)-cis-N-methylcanadine + NADPH + O2
allocryptopine + NADP+ + H2O
(S)-cis-N-methylcorydalmine + NADPH + O2
muramine + NADP+ + H2O
Corydalis vaginans
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?
(S)-cis-N-methylstylopine + NADPH + O2
protopine + NADP+ + H2O
Corydalis vaginans
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(S)-cis-N-methyltetrahydropalmitine + NADPH + O2
muramine + NADP+ + H2O
Corydalis vaginans
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(S)-cis-N-methyltetrahydrothalifendine + NADPH + O2
thalictrisine + NADP+ + H2O
Corydalis vaginans
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(S)-cis-N-methylcanadine + NADPH + O2

allocryptopine + NADP+ + H2O
Corydalis vaginans
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no activity without molecular oxygen
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(S)-cis-N-methylcanadine + NADPH + O2
allocryptopine + NADP+ + H2O
Corydalis vaginans
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(R)-cis/trans-N-methyl-canadine is no substrate
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?
(S)-cis-N-methylcanadine + NADPH + O2
allocryptopine + NADP+ + H2O
Corydalis vaginans
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hydroxylation in benzylisoquinoline metabolism
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?
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(S)-cis-N-methylcanadine + NADPH + O2
allocryptopine + NADP+ + H2O
(S)-cis-N-methylcanadine + NADPH + O2

allocryptopine + NADP+ + H2O
Corydalis vaginans
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(R)-cis/trans-N-methyl-canadine is no substrate
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?
(S)-cis-N-methylcanadine + NADPH + O2
allocryptopine + NADP+ + H2O
Corydalis vaginans
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hydroxylation in benzylisoquinoline metabolism
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?
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cytochrome P450
Corydalis vaginans
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NADH
Corydalis vaginans
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33% of the activity with NADPH, NAD+ or NADP+ are ineffective
NADPH
Corydalis vaginans
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Ancymidol
Corydalis vaginans
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CO
Corydalis vaginans
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reversible by light
cytochrome c
Corydalis vaginans
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ketoconazole
Corydalis vaginans
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Metyrapone
Corydalis vaginans
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Prochloraz
Corydalis vaginans
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0.0125
cis-N-methylcanadine
Corydalis vaginans
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0.0625
NADPH
Corydalis vaginans
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0.0255
Corydalis vaginans
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8.5
Corydalis vaginans
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6.5 - 9.7
Corydalis vaginans
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half-maximal activity at pH 6.5 and pH 9.7
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30
Corydalis vaginans
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10 - 45
Corydalis vaginans
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half-maximal activity at 10°C and 45°C
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Corydalis vaginans
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brenda
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Corydalis vaginans
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membrane bound
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brenda
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MSH_PAPSO
526
59346
Swiss-Prot
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Rueffer, M.; Zenk, M.H.
Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans
Tetrahedron Lett.
28
5307-5310
1987
Corydalis vaginans
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brenda
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