Information on EC 1.14.19.50 - noroxomaritidine synthase

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The expected taxonomic range for this enzyme is: Narcissus aff. pseudonarcissus MK-2014

EC NUMBER
COMMENTARY hide
1.14.19.50
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RECOMMENDED NAME
GeneOntology No.
noroxomaritidine synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2 = (4aR,10bS)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(1)
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4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2 = (4aS,10bR)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(2)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Amaryllidacea alkaloids biosynthesis
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Isoquinoline alkaloid biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
4'-O-methylnorbelladine,NADPH—hemoprotein reductase:oxygen oxidoreductase (noroxomaritidine-forming)
A P-450 (heme-thiolate) enzyme. The enzyme, characterized from Narcissus pseudonarcissus (daffodil), forms the two enantiomers of the Amaryllidacea alkaloid noroxomaritidine by catalysing intramolecular oxidative para-para' phenol coupling. The oxidation involves molecular oxygen without its incorporation into the product.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
CYP96T1 catalyzes the first major branch in Amaryllidaceae alkaloid biosynthesis
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2) 4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
(4aS,10bR)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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formation of the para-ortho' phenol coupled product, N-demethylnarwedine, at less than 1% of the total product
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?
(R)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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-
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?
(S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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-
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?
4'-O-methyl-N-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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?
4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
(4aR,10bS)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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formation of the para-ortho' phenol coupled product, N-demethylnarwedine, at less than 1% of the total product
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?
additional information
?
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the enzyme catalyzes a C-C phenol-coupling reaction with para-para’ regiospecificity. No substrates: norbelladine, N-methylnorbelladine, 3'-O-methylnorbelladine, 3',4'-O-dimethylnorbelladine
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4'-O-methyl-N-methylnorbelladine
substrate inhibition
4'-O-methylnorbelladine
substrate inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.659
(R)-coclaurine
pH 8.0, 30°C
0.637
(S)-Coclaurine
pH 8.0, 30°C
0.00328
4'-O-methyl-N-methylnorbelladine
pH 8.0, 30°C
0.00113
4'-O-methylnorbelladine
pH 8.0, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.035
(R)-coclaurine
pH 8.0, 30°C
0.022
(S)-Coclaurine
pH 8.0, 30°C
0.041
4'-O-methyl-N-methylnorbelladine
pH 8.0, 30°C
0.25
4'-O-methylnorbelladine
pH 8.0, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.053
(R)-coclaurine
pH 8.0, 30°C
0.035
(S)-Coclaurine
pH 8.0, 30°C
12.37
4'-O-methyl-N-methylnorbelladine
pH 8.0, 30°C
216.7
4'-O-methylnorbelladine
pH 8.0, 30°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.174
4'-O-methyl-N-methylnorbelladine
pH 8.0, 30°C
0.064
4'-O-methylnorbelladine
pH 8.0, 30°C