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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
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T6ODM
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thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
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thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2
spontaneous conversion of neopinione to codeinone
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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.
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(R,S)-canadine + 2-oxoglutarate + O2
?
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a protoberberine, 32% of activity with oripavine
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-
?
(R,S)-tetrahydropalmatine + 2-oxoglutarate + O2
?
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a protoberberine, O-demethylation, below 1% of activity with oripavine
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-
?
(R,S)-tetrahydropapaverine + 2-oxoglutarate + O2
?
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a 1-benzylisoquinoline, O-demethylation, 2.1% of activity with oripavine
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-
?
allocryptopine + 2-oxoglutarate + O2
?
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a protopine, O-demethylation, 9.5% of activity with oripavine
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-
?
cryptopine + 2-oxoglutarate + O2
?
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a protopine, O-demethylation, below 1% of activity with oripavine
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-
?
oripavine + 2-oxoglutarate + O2
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a morphinan, best substrate
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-
?
oripavine + 2-oxoglutarate + O2
morphinane + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
papaverine + 2-oxoglutarate + O2
?
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a 1-benzylisoquinoline,O-demethylation, below 1% of activity with oripavine
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-
?
thebaine + 2-oxoglutarate + O2
codeinone + formaldehyde + succinate + CO2
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-
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
additional information
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oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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a step of morphine biosynthesis
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-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde
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-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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-
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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a step of morphine biosynthesis
spontaneous conversion to codeinone
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?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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85% of the activity with oripavine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde
spontaneous conversion to codeinone
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?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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a morphinan, 97.2% of activity with oripavine
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-
?
additional information
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no activity with (S)-reticuline, (S)-scoulerine, papaverine, (S)-corytuberine, pavine, salutaridine, noscapine, codeine
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additional information
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when assayed with a wide range of benzylisoquinoline alkaloids, the enzyme shows efficient dealkylation activities, including regio- and substrate-specific O-demethylation and O,O-demethylenation, substrate specificity, overview. No or poor activity with (S)-reticuline, (S)-isocorydine, (S)-scoulerine, (R,S)-stylopine, berberine, O-demethylcryptopine, protopine, and codeine
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oripavine + 2-oxoglutarate + O2
morphinane + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
thebaine + 2-oxoglutarate + O2
codeinone + formaldehyde + succinate + CO2
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-
-
-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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-
-
-
?
oripavine + 2-oxoglutarate + O2
morphinone + formaldehyde + succinate + CO2
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a step of morphine biosynthesis
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-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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-
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-
?
thebaine + 2-oxoglutarate + O2
neopinone + formaldehyde + succinate + CO2
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a step of morphine biosynthesis
spontaneous conversion to codeinone
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?
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0.0164
2-oxoglutarate
-
pH 7.4, 30°C
0.0154
oripavine
-
pH 7.4, 30°C
0.0203
thebaine
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pH 7.4, 30°C
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0.0081
2-oxoglutarate
-
pH 7.4, 30°C
0.0191
oripavine
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pH 7.4, 30°C
0.017
thebaine
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pH 7.4, 30°C
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492.9
2-oxoglutarate
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pH 7.4, 30°C
1243
oripavine
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pH 7.4, 30°C
837.1
thebaine
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pH 7.4, 30°C
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0.518
thebaine
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pH 7.4, 30°C
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brenda
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brenda
cv. Bea's Choice
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brenda
high-morphine varieties (i.e. L, 11 and 40) and a mutant variety (i.e. T) that accumulates high levels of thebaine and oripavine, but lacks morphine and codeine
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brenda
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brenda
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evolution
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the enzyme belongs to the 2-oxoglutarate/Fe(II)-dependent dioxygenase superfamily
malfunction
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virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine
metabolism
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thebaine 6-O-demethylase catalyzes the antepenultimate step of morphine biosynthesis in opium poppy
physiological function
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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
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DIOX1_PAPSO
364
0
40624
Swiss-Prot
A0A396GPI6_MEDTR
86
0
9573
TrEMBL
A0A396GMK1_MEDTR
62
0
6773
TrEMBL
A0A2G9G071_9LAMI
177
0
20294
TrEMBL
A0A072UFL7_MEDTR
352
0
40073
TrEMBL
A0A072TL01_MEDTR
353
0
39919
TrEMBL
A0A2G9HXH5_9LAMI
352
0
39543
TrEMBL
A0A396JBY5_MEDTR
384
0
44304
TrEMBL
A0A2G9GHQ2_9LAMI
356
0
39749
TrEMBL
A0A396GME6_MEDTR
131
0
14765
TrEMBL
A0A072UER0_MEDTR
353
0
40116
TrEMBL
A0A396JDV8_MEDTR
334
0
38451
TrEMBL
A0A072U060_MEDTR
370
0
42309
TrEMBL
A0A396GYS0_MEDTR
457
0
52785
TrEMBL
A0A2G9GZ15_9LAMI
97
0
11063
TrEMBL
A0A2P6Q562_ROSCH
310
0
35449
TrEMBL
A0A2P6RV84_ROSCH
301
0
34112
TrEMBL
A0A2G9GVE4_9LAMI
350
0
40260
TrEMBL
A0A2G9GYU2_9LAMI
358
0
40269
TrEMBL
A0A396GUN0_MEDTR
355
0
40376
TrEMBL
A0A072TJA3_MEDTR
261
0
29948
TrEMBL
A0A2G9HXH1_9LAMI
166
0
18652
TrEMBL
A0A072VFZ2_MEDTR
358
0
40386
TrEMBL
A0A396HYT1_MEDTR
379
0
43699
TrEMBL
A0A396GMH7_MEDTR
365
0
41266
TrEMBL
A0A2G9GGH5_9LAMI
355
0
40034
TrEMBL
A0A396GMQ9_MEDTR
371
0
42136
TrEMBL
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His6-tagged protein is produced in Escherichia coli
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phylogenetic tree, T6ODM real time quantitative PCR expression analysis
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endophyte SM3B (Marmoricola sp.) can enhance enzyme expression by 2.5fold
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enzyme expression is significantly up-regulated with methyl jasmonate and salicylic acid treatments at 48 h
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Hagel, J.M.; Facchini, P.J.
Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy.
Nat. Chem. Biol.
6
273-275
2010
Papaver somniferum
brenda
Farrow, S.C.; Facchini, P.J.
Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy
J. Biol. Chem.
288
28997-29012
2013
Papaver somniferum
brenda
Hashemi, S.; Naghavi, M.
Production and gene expression of morphinan alkaloids in hairy root culture of Papaver orientale L. using abiotic elicitors
Plant Cell
125
31-41
2016
Papaver orientale
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brenda
Pandey, S.S.; Singh, S.; Babu, C.S.; Shanker, K.; Srivastava, N.K.; Kalra, A.
Endophytes of opium poppy differentially modulate host plant productivity and genes for the biosynthetic pathway of benzylisoquinoline alkaloids
Planta
243
1097-1114
2016
Papaver somniferum
brenda
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1.14.11.31 thebaine 6-O-demethylase
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