Information on EC 1.13.99.3 - tryptophan 2'-dioxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.13.99.3
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RECOMMENDED NAME
GeneOntology No.
tryptophan 2'-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + O2 = (indol-3-yl)glycolaldehyde + CO2 + NH3
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Tryptophan metabolism
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tryptophan metabolism
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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan:oxygen 2'-oxidoreductase (side-chain-cleaving)
A hemoprotein. Acts on a number of indole-3-alkane derivatives, oxidizing the 3-side-chain in the 2'-position. Best substrates were L-tryptophan and 5-hydroxy-L-tryptophan.
CAS REGISTRY NUMBER
COMMENTARY hide
64295-81-4
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90371-50-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
strain HP72
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Manually annotated by BRENDA team
strain XA
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-indoleacetaldehyde + O2
?
show the reaction diagram
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-
-
-
?
3-indoleacetamide + O2
?
show the reaction diagram
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-
-
-
?
3-indolelactate + O2
?
show the reaction diagram
3-indolemethanol + O2
?
show the reaction diagram
3-indolepropionate + O2
?
show the reaction diagram
3-indolepyruvate + O2
?
show the reaction diagram
-
-
-
-
?
3-indolethanol + O2
?
show the reaction diagram
3-methylindole + O2
3-indolecarboxaldehyde + H2O
show the reaction diagram
5-hydroxy-L-tryptophan + O2
?
show the reaction diagram
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-
-
-
?
5-hydroxytryptamine + O2
?
show the reaction diagram
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-
-
-
?
5-methyl-DL-tryptophan + O2
?
show the reaction diagram
-
-
-
-
?
alpha-hydroxy-L-tryptophan + O2
?
show the reaction diagram
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-
-
-
?
D-tryptophan + O2
?
show the reaction diagram
DL-5-fluorotryptophan + O2
?
show the reaction diagram
-
-
-
-
?
hormone-releasing factor + O2
?
show the reaction diagram
-
-
-
-
?
indole-3-butyric acid + O2
?
show the reaction diagram
-
-
-
-
?
L-Trp-L-Phe + O2 + O2
?
show the reaction diagram
-
-
-
-
?
L-Trp-L-Trp + O2
?
show the reaction diagram
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-
-
-
?
L-tryptophan + O2
3-indoleglycolaldehyde + CO2 + NH3
show the reaction diagram
L-tryptophan methyl ester + O2
?
show the reaction diagram
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-
-
-
?
Leu-Trp + O2
Leu-alpha,beta-dehydrotryptamine + CO2 + H2O
show the reaction diagram
Leu-Trp-Leu + O2
?
show the reaction diagram
Leu-Trp-Leu + O2
Leu-beta-hydroxy-Trp-Leu + Leu-beta-hydroxy-Trp-Leu + Leu-alpha,beta-dehydro-Trp-Leu + ?
show the reaction diagram
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ratio of products depends on pH and ionic strength
?
melatonin + O2
?
show the reaction diagram
N-acetyl-L-tryptophan + O2
?
show the reaction diagram
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-
-
-
?
N-acetyl-L-tryptophanamide + O2
beta-keto-N-acetyltryptophanamide + H2O
show the reaction diagram
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
show the reaction diagram
N-acetylacetamide + O2
?
show the reaction diagram
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-
-
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?
Trp-Leu + O2
threo-beta-hydroxytryptophan + erythro-beta-hydroxytryptophan + ?
show the reaction diagram
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-
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?
tryptamine + O2
?
show the reaction diagram
tryptophan + O2
indolyloxazoline + H2O
show the reaction diagram
additional information
additional information
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-tryptophan + O2
3-indoleglycolaldehyde + CO2 + NH3
show the reaction diagram
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first enzyme of metabolic pathway for tryptophan
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
hydroxylamine
indole-3-methanol
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inhibits oxidation of skatole
Skatole
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inhibits oxidation of indole-3-methanol
Sodium azide
Sodium nitrite
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almost completely at 1 mM, TSO I and II, not: dehydrogenase component
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0435 - 0.055
3-indolemethanol
0.0154 - 0.025
3-Methylindole
0.67
ferricyanide
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0.48
indole-3-methanol
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0.0015 - 0.01
L-tryptophan
0.1 - 0.12
N-Acetyl-L-tryptophanamide
0.05 - 0.055
O2
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 7
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broad, TSO II with N-acetyl-L-tryptophanamide, ferricyanide reductase activity of TSO II and dehydrogenase component
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
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x * 64000 + x * 40000 + x + 35000 + x * 28000, TSO I, SDS-PAGE
40000
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x * 64000 + x * 40000 + x + 35000 + x * 28000, TSO I, SDS-PAGE
64000
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x * 64000 + x * 40000 + x + 35000 + x * 28000, TSO I, SDS-PAGE
150000
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TSO II; TSO II, gel filtration
250000
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sedimentation equilibrium ultracentrifugation
280000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 64000 + x * 40000 + x + 35000 + x * 28000, TSO I, SDS-PAGE; x * 72000 + x * 48000, TSO II, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
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TSO II, 10 min, pH 6.0, 70% loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, several months
0C, pH 6, stable in presence of either 80% ethyl alcohol, 6 M urea or 0.5% SDS for at least 6 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dehydrogenase component and oxidase component
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TSO I and TSO II as well as dehydrogenase component and oxidase component of TSO II
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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use for tryptophan depletion in patients with refractory acute lymphocytic leukemia