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Literature summary for 1.14.11.31 extracted from

  • Hagel, J.M.; Facchini, P.J.
    Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. (2010), Nat. Chem. Biol., 6, 273-275.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
His6-tagged protein is produced in Escherichia coli Papaver somniferum

Inhibitors

Inhibitors Comment Organism Structure
thebaine
-
Papaver somniferum

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0154
-
oripavine pH 7.4, 30°C Papaver somniferum
0.0164
-
2-oxoglutarate pH 7.4, 30°C Papaver somniferum
0.0203
-
thebaine pH 7.4, 30°C Papaver somniferum

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ required Papaver somniferum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
oripavine + 2-oxoglutarate + O2 Papaver somniferum a step of morphine biosynthesis morphinone + formaldehyde + succinate + CO2
-
?
thebaine + 2-oxoglutarate + O2 Papaver somniferum a step of morphine biosynthesis neopinone + formaldehyde + succinate + CO2 spontaneous conversion to codeinone ?

Organism

Organism UniProt Comment Textmining
Papaver somniferum
-
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
-

Purification (Commentary)

Purification (Comment) Organism
-
Papaver somniferum

Reaction

Reaction Comment Organism Reaction ID
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2 spontaneous conversion of neopinione to codeinone Papaver somniferum

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information no activity with (S)-reticuline, (S)-scoulerine, papaverine, (S)-corytuberine, pavine, salutaridine, noscapine, codeine Papaver somniferum ?
-
?
oripavine + 2-oxoglutarate + O2 a step of morphine biosynthesis Papaver somniferum morphinone + formaldehyde + succinate + CO2
-
?
oripavine + 2-oxoglutarate + O2 alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde Papaver somniferum morphinone + formaldehyde + succinate + CO2
-
?
thebaine + 2-oxoglutarate + O2 a step of morphine biosynthesis Papaver somniferum neopinone + formaldehyde + succinate + CO2 spontaneous conversion to codeinone ?
thebaine + 2-oxoglutarate + O2 85% of the activity with oripavine. Alkyl hydroxylation proceeds through a radical mechanism involving an iron-oxo intermediate, followed by the elimination of formaldehyde Papaver somniferum neopinone + formaldehyde + succinate + CO2 spontaneous conversion to codeinone ?

Synonyms

Synonyms Comment Organism
T6ODM
-
Papaver somniferum

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Papaver somniferum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0081
-
2-oxoglutarate pH 7.4, 30°C Papaver somniferum
0.017
-
thebaine pH 7.4, 30°C Papaver somniferum
0.0191
-
oripavine pH 7.4, 30°C Papaver somniferum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Papaver somniferum

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.518
-
thebaine pH 7.4, 30°C Papaver somniferum

General Information

General Information Comment Organism
malfunction virus-induced gene silencing of T6ODM in opium poppy efficiently blocks metabolism at thebaine Papaver somniferum

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
492.9
-
2-oxoglutarate pH 7.4, 30°C Papaver somniferum
837.1
-
thebaine pH 7.4, 30°C Papaver somniferum
1243
-
oripavine pH 7.4, 30°C Papaver somniferum