Information on EC 1.14.13.55 - protopine 6-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.55
-
RECOMMENDED NAME
GeneOntology No.
protopine 6-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
protopine + NADPH + H+ + O2 = 6-hydroxyprotopine + NADP+ + H2O
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
sanguinarine and macarpine biosynthesis
-
-
Isoquinoline alkaloid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
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-
SYSTEMATIC NAME
IUBMB Comments
protopine,NADPH:oxygen oxidoreductase (6-hydroxylating)
A heme-thiolate protein (P-450) involved in benzophenanthridine alkaloid synthesis in higher plants.
CAS REGISTRY NUMBER
COMMENTARY hide
128561-60-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Berberis stolonifera
elicited and non-elicited cells
-
-
Manually annotated by BRENDA team
no activity in Catharanthus roseus
elicited and non-elicited cells
-
-
Manually annotated by BRENDA team
opium poppy
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
13-oxoprotopine + NADPH + O2
?
show the reaction diagram
-
-
-
?
allocryptopine + NADPH + H+ + O2
6-hydroxyallocryptopine + NADP+ + H2O
show the reaction diagram
-
-
-
?
corycavine + NADPH + H+ + O2
corynoloxine + NADP+ + H2O
show the reaction diagram
-
-
-
?
protopine + NADPH + H+ + O2
6-hydroxyprotopine + NADP+ + H2O
show the reaction diagram
Protopine + NADPH + O2
Dihydrosanguinarine + NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
protopine + NADPH + H+ + O2
6-hydroxyprotopine + NADP+ + H2O
show the reaction diagram
-
hydroxylation of protopine by protopine 6-hydroxylase produces the unstable intermediate 6-hydroxyprotopine that spontaneously rearranges to form dihydrosanguinarine
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-
ir
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
the enzyme is linked to cytochrome P-450
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NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome c
-
-
ketoconazole
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0087
6-hydroxyallocryptopine
in 50 mM HEPES/NaOH (pH 7.6), at 30C
-
0.00645
6-hydroxyprotopine
in 50 mM HEPES/NaOH (pH 7.6), at 30C
0.002
protopine
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 8.5
-
pH 6.3: about 35% of maximal activity, pH 8.5: about 40% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 40
-
about 50% of maximal actvity at 10C and 40C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae