Information on EC 1.14.11.31 - thebaine 6-O-demethylase

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The expected taxonomic range for this enzyme is: Papaver somniferum

EC NUMBER
COMMENTARY hide
1.14.11.31
-
RECOMMENDED NAME
GeneOntology No.
thebaine 6-O-demethylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
morphine biosynthesis
-
-
Isoquinoline alkaloid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating)
Requires Fe2+. Catalyses a step in morphine biosynthesis. The product neopinione spontaneously rearranges to the more stable codeinone. The enzyme also catalyses the 6-O-demethylation of oripavine to morphinone, with lower efficiency.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily
malfunction
-
virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine
metabolism
-
thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy
physiological function
-
thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy, but has also roles in the metabolism of protopine, benzo[c]phenanthridine, and rhoeadine alkaloids
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R,S)-canadine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a protoberberine, 32% of activity with oripavine
-
-
?
(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a protoberberine, O-demethylation, below 1% of activity with oripavine
-
-
?
(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine
-
-
?
allocryptopine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a protopine, O-demethylation, 9.5% of activity with oripavine
-
-
?
cryptopine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a protopine, O-demethylation, below 1% of activity with oripavine
-
-
?
oripavine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a morphinan, best substrate
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
show the reaction diagram
papaverine + 2-oxoglutarate + O2
?
show the reaction diagram
-
a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
show the reaction diagram
-
a step of morphine biosynthesis
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
thebaine
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0164
2-oxoglutarate
-
pH 7.4, 30C
0.0154
oripavine
-
pH 7.4, 30C
0.0203
thebaine
-
pH 7.4, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0081
2-oxoglutarate
Papaver somniferum
-
pH 7.4, 30C
0.0191
oripavine
Papaver somniferum
-
pH 7.4, 30C
0.017
thebaine
Papaver somniferum
-
pH 7.4, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
492.9
2-oxoglutarate
Papaver somniferum
-
pH 7.4, 30C
34
1243
oripavine
Papaver somniferum
-
pH 7.4, 30C
9237
837.1
thebaine
Papaver somniferum
-
pH 7.4, 30C
4569
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.518
thebaine
-
pH 7.4, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
His6-tagged protein is produced in Escherichia coli
-
phylogenetic tree, T6ODM real time quantitative PCR expression analysis
-