Information on EC 1.14.19.50 - noroxomaritidine synthase

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The enzyme appears in viruses and cellular organisms

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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-
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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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-
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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
Narcissus sp. aff. pseudonarcissus
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UniProt
Manually annotated by BRENDA team
Narcissus sp. aff. pseudonarcissus MK-2014
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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
(R)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(S)-coclaurine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
4'-O-methyl-N-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
4'-O-methylnorbelladine + [reduced NADPH-hemoprotein reductase] + O2
(4aR,10bS)-noroxomaritidine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
Narcissus sp. aff. pseudonarcissus
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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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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
substrate inhibition
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
substrate inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.659
(R)-coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.637
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.00328
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.00113
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.035
(R)-coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.022
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.041
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.25
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.053
(R)-coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.035
(S)-Coclaurine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
12.37
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
216.7
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.174
4'-O-methyl-N-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C
0.064
4'-O-methylnorbelladine
Narcissus sp. aff. pseudonarcissus
pH 8.0, 30°C