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Information on EC 1.14.14.98 - protopine 6-monooxygenase
for references in articles please use BRENDA:EC1.14.14.98
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.98 protopine 6-monooxygenase
IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein involved in benzophenanthridine alkaloid synthesis in higher plants.
The enzyme appears in viruses and cellular organisms
- 1.14.14.98
- sanguinarine
- somniferum
-
papaver
-
benzylisoquinoline
- papaveraceae
- elicitors
- stylopine
- alkaloids
- allocryptopine
Reaction Schemes
showSynonyms
protopine 6-hydroxylase, cyp82n2v2, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 1.14.13.55
-
-
formerly
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Oxygenase, protropine 6-mono-
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-
-
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P6H
protopine 6-hydroxylase
Protopine-6-hydroxylase
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-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
protopine + [reduced NADPH-hemoprotein reductase] + O2 = 6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
sanguinarine and macarpine biosynthesis
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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.
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CAS REGISTRY NUMBER
COMMENTARY
128561-60-4
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
13-oxoprotopine + [reduced NADPH-hemoprotein reductase] + O2
?
Substrates: -
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?
allocryptopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyallocryptopine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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?
corycavine + [reduced NADPH-hemoprotein reductase] + O2
corynoloxine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
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Products: -
?
protopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
protopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: i.e. dihydrosanguinarine
Products: -
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?
protopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: hydroxylation of protopine by protopine 6-hydroxylase produces the unstable intermediate 6-hydroxyprotopine that spontaneously rearranges to form dihydrosanguinarine
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protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: -
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Products: -
?
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
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?
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
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?
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
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?
protopine + [reduced NADPH-hemoprotein reductase] + O2
dihydrosanguinarine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
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?
additional information
?
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Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
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?
additional information
?
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Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
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?
additional information
?
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Substrates: no activity with protopine-N-oxide, reticuline, scoulerine, and N-methyl stylopine
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additional information
?
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Substrates: no activity with protopine-N-oxide, reticuline, scoulerine, and N-methyl stylopine
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
protopine + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyprotopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: hydroxylation of protopine by protopine 6-hydroxylase produces the unstable intermediate 6-hydroxyprotopine that spontaneously rearranges to form dihydrosanguinarine
Products: -
Products: -
ir
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
additional information
?
-
-
Substrates: the enzyme is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0087
6-hydroxyallocryptopine
in 50 mM HEPES/NaOH (pH 7.6), at 30Ā°C
0.00645
6-hydroxyprotopine
in 50 mM HEPES/NaOH (pH 7.6), at 30Ā°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.3 - 8.5
-
pH 6.3: about 35% of maximal activity, pH 8.5: about 40% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
weak activity in non-elicited cells, higher activity in elicited cells
brenda
-
weak activity in non-elicited cells, higher activity in elicited cells
brenda
-
weak activity in non-elicited cells, higher activity in elicited cells
brenda
-
weak activity in non-elicited cells, higher activity in elicited cells
brenda
-
weak activity in non-elicited cells, higher activity in elicited cells
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is involved in the benzylisoquinoline alkaloid pathway
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). P6H_ESCCA
524
3
59462
Swiss-Prot
Secretory Pathway (Reliability: 1)
P6H_PAPSO
541
1
61438
Swiss-Prot
Secretory Pathway (Reliability: 1)
A0A2P6SIG6_ROSCH
137
0
15479
TrEMBL
other Location (Reliability: 4)
A0A2P6QH88_ROSCH
67
0
7313
TrEMBL
other Location (Reliability: 3)
A0A2P6SII7_ROSCH
79
0
9366
TrEMBL
other Location (Reliability: 3)
A0A1W6S9Y7_CHEMJ
259
2
29162
TrEMBL
Secretory Pathway (Reliability: 2)
A0A2P6PYF8_ROSCH
152
0
16973
TrEMBL
other Location (Reliability: 3)
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
when culture filtrate of the endophytic fungus Tichoderma harzanium is employed along with 0.050 mM shikimate on embryogenic cell suspensions of latex-less Papaver somniferum a 8-9fold increase in protopine 6-hydroxylase transcripts is observed
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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
-
brenda
Beaudoin, G.; Facchini, P.
Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis
Biochem. Biophys. Res. Commun.
431
597-603
2013
Papaver somniferum
brenda
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
brenda
Verma, P.; Khan, S.A.; Mathur, A.K.; Ghosh, S.; Shanker, K.; Kalra, A.
Improved sanguinarine production via biotic and abiotic elicitations and precursor feeding in cell suspensions of latex-less variety of Papaver somniferum with their gene expression studies and upscaling in bioreactor
Protoplasma
251
1359-1371
2014
Papaver somniferum (L7X0L7), Papaver somniferum
brenda
EXTERNAL LINKS (specific for EC-Number 1.14.14.98)
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Release 2023.1 (January 2023)
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