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Information on EC 1.14.14.98 - protopine 6-monooxygenase and Organism(s) Eschscholzia californica and UniProt Accession F2Z9C1

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein involved in benzophenanthridine alkaloid synthesis in higher plants.
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Select one or more organisms in this record: ?
This record set is specific for:
Eschscholzia californica
UNIPROT: F2Z9C1
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Word Map
The taxonomic range for the selected organisms is: Eschscholzia californica
The enzyme appears in selected viruses and cellular organisms
Synonyms
protopine 6-hydroxylase, cyp82n2v2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
protopine 6-hydroxylase
-
Oxygenase, protropine 6-mono-
-
-
-
-
Protopine-6-hydroxylase
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
protopine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein involved in benzophenanthridine alkaloid synthesis in higher plants.
CAS REGISTRY NUMBER
COMMENTARY hide
128561-60-4
-
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 + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
allocryptopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyallocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
corycavine + [reduced NADPH-hemoprotein reductase] + O2
corynoloxine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
protopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
i.e. dihydrosanguinarine
-
-
?
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
the enzyme is linked to cytochrome P-450
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ketoconazole
less than 2% activity at 0.025 mM
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 30°C
0.00645
6-hydroxyprotopine
in 50 mM HEPES/NaOH (pH 7.6), at 30°C
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 activity at 10°C and 40°C
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
california poppy
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
weak activity in non-elicited cells, higher activity in elicited cells
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
membrane-bound
-
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
P6H_ESCCA
524
3
59462
Swiss-Prot
Secretory Pathway (Reliability: 1)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Tanahashi, T.; Zenk, M.H.
Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis
Phytochemistry
29
1113-1122
1990
Chelidonium majus, Dicentra cucullaria, Eschscholzia californica, Eschscholzia lobbii, Fumaria parviflora, no activity in Berberis stolonifera, no activity in Catharanthus roseus
-
Manually annotated by BRENDA team
Takemura, T.; Ikezawa, N.; Iwasa, K.; Sato, F.
Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells
Phytochemistry
91
100-108
2013
Eschscholzia californica (F2Z9C1), Eschscholzia californica
Manually annotated by BRENDA team