Information on EC 1.14.13.125 - tryptophan N-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.125
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RECOMMENDED NAME
GeneOntology No.
tryptophan N-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + 2 O2 + 2 NADPH + 2 H+ = (E)-indol-3-ylacetaldoxime + 2 NADP+ + CO2 + 3 H2O
show the reaction diagram
overall reaction
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L-tryptophan + O2 + NADPH + H+ = N-hydroxy-L-tryptophan + NADP+ + H2O
show the reaction diagram
(1a)
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N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O
show the reaction diagram
(1c)
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N-hydroxy-L-tryptophan + O2 + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O
show the reaction diagram
(1b)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Tryptophan metabolism
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Glucosinolate biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan,NADPH:oxygen oxidoreductase (N-hydroxylating)
A heme-thiolate protein (P-450). This enzyme catalyses two successive N-hydroxylations of L-tryptophan, the first steps in the biosynthesis of both auxin and the indole alkaloid phytoalexin camalexin. The product of the two hydroxylations, N,N-dihydroxy-L-tryptophan, is extremely labile and dehydrates spontaneously. The dehydrated product is then subject to a decarboxylation that produces an oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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
L-tryptophan + NADPH + H+
indole-3-acetaldoxime + NADP+ + CO2 + H2O
show the reaction diagram
L-tryptophan + NADPH + H+ + O2
indole-3-acetaldoxime + NADP+ + CO2 + H2O
show the reaction diagram
additional information
?
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CYP79B1 is not able to metabolize L-phenylalanine or L-tyrosine
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-aminobenzotriazole
the activity of CYP79B2 is inhibited 18 and 75% by 0.4 mM and 4 mM 1-aminobenzotriazole
2,4-Dichlorophenol
800 mM 2,4-dichlorophenol added to the CYP79B2 reconstitution assay inhibits the activity by 72%
H2O2
100 mM H2O2 added to the CYP79B2 reconstitution assay inhibits the activity by 96%
MnCl2
1 mM MnCl2 added to the CYP79B2 reconstitution assay inhibits the activity by 34%
tetcyclasis
the activity of CYP79B2 is inhibited 54 and 76% by 0.02 and 0.2 mM tetcyclasis
additional information
CYP79B2 is not inhibited by Me2SO of a maximum concentration of 4% (v/v); the combination of 100 mM H2O2, 1 mM MnCl2, and 800 mM 2,4-dichlorophenol added to the reconstitution assay inhibits the CYP79B2 activity by 99%
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.021 - 0.029
L-tryptophan
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
highest expression in roots
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
61000
estimated from amino acid sequence
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli C43(DE3) cells
expressed in Escherichia coli C43(DE3) cells, reconstitution of CYP79B1 monooxygenase requires a NADPH:cytochrome P450 reductase
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expressed in Escherichia coli; expressed in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP79B2 expression is induced up to 1.5fold by wounding, 2.8fold by 0.25 mM methyl jasmonate in combination with 2.5 mM 1-aminocyclopropane-1-carboxylate, and 4.6fold after methyl jasmonate treatment alone. CYP79B3 is induced 3.5fold by methyl jasmonate and up to 1.7fold by methyl jasmonate in combination with 1-aminocyclopropane-1-carboxylate, and the induction levels are lower than those observed for CYP79B2. After treatment with 0.0002 mM 2,4-dichloro-phenoxyacetic acid, expression of CYP79B2 and CYP79B3 is induced 1.6 and 1.3fold, respectively
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CYP79B2 is wound-inducible
induction of the CYP79B2 mRNA levels is observed 12.5 h after infection by virulent strain Pseudomonas syringae pv. maculicola
the basal expression level of CYP79B3 is suppressed to 0.6fold that of control levels by 1-aminocyclopropane-1-carboxylate treatment
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the transcript level of CYP79B2, but not CYP79B3, is increased 3fold upon induction of camalexin by silver nitrate
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