1.13.99.3: tryptophan 2'-dioxygenase
This is an abbreviated version!
For detailed information about tryptophan 2'-dioxygenase, go to the full flat file.
Word Map on EC 1.13.99.3
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1.13.99.3
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indole-3-acetic
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tryptamine
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pyrrolnitrin
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indole-3-acetamide
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2,4-diacetylphloroglucinol
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diastereoisomeric
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indole-3-carboxaldehyde
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3-substituted
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medicine
- 1.13.99.3
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indole-3-acetic
- tryptamine
- pyrrolnitrin
- indole-3-acetamide
- 2,4-diacetylphloroglucinol
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diastereoisomeric
- indole-3-carboxaldehyde
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3-substituted
- medicine
Reaction
Synonyms
indole-3-alkane alpha-hydroxylase, indolyl-3-alkane alpha-hydroxylase, oxidase, tryptophan side-chain alpha,beta-, oxidase, tryptophan side-chain alpha,beta-, II, tryptophan side chain oxidase, tryptophan side chain oxidase II, tryptophan side chain oxidase type I, tryptophan side-chain alpha,beta-oxidase, tryptophan side-chain oxidase, TSO, TSO I, TSO II, TSOII
ECTree
1.13.99.3 tryptophan 2'-dioxygenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.13.99.3 - tryptophan 2'-dioxygenase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
Leu-Trp-Leu + O2
Leu-beta-hydroxy-Trp-Leu + Leu-beta-hydroxy-Trp-Leu + Leu-alpha,beta-dehydro-Trp-Leu + ?
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ratio of products depends on pH and ionic strength
?
Trp-Leu + O2
threo-beta-hydroxytryptophan + erythro-beta-hydroxytryptophan + ?
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?
3-methylindole + O2
3-indolecarboxaldehyde + H2O
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intermediate: 3-indolemethanol, under anaerobic conditions with ferricyanide
?
3-methylindole + O2
3-indolecarboxaldehyde + H2O
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O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
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?
3-methylindole + O2
3-indolecarboxaldehyde + H2O
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3-methylindole is skatole, two-step sequential reactions
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?
L-tryptophan + O2
3-indoleglycolaldehyde + CO2 + NH3
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-
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?
L-tryptophan + O2
3-indoleglycolaldehyde + CO2 + NH3
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O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
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?
L-tryptophan + O2
3-indoleglycolaldehyde + CO2 + NH3
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first enzyme of metabolic pathway for tryptophan
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?
Leu-Trp + O2
Leu-alpha,beta-dehydrotryptamine + CO2 + H2O
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O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
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-
?
N-acetyl-L-tryptophanamide + O2
beta-keto-N-acetyltryptophanamide + H2O
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two-step sequential reactions, below pH 5.8, O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
intermediate: beta-hydroxy erythro- and threo-N-acetyl-L-tryptophanamide
?
N-acetyl-L-tryptophanamide + O2
beta-keto-N-acetyltryptophanamide + H2O
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-
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
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above pH 5.8, O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
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-
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
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-
-
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
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main product, intermediate is 5-(3-indolyl)-2-methyl-2-oxazoline-4-carboxamide
?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O
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-
-
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?
tryptophan + O2
indolyloxazoline + H2O
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internally located tryptophan, O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
further formation of alpha,beta-didehydrotryptophan residue (after isomerization) or a diastereomeric mixture of beta-hydroxytryptophan residues (after hydration)
?
tryptophan + O2
indolyloxazoline + H2O
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internally located tryptophan, O2 required, 2,6-dichlorophenolindophenol and ferricyanide replace O2
further formation of alpha,beta-didehydrotryptophan residue (after isomerization) or a diastereomeric mixture of beta-hydroxytryptophan residues (after hydration)
?
additional information
additional information
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substrate: yeast mating hormone (alpha-factor)
with any substrate 3-indolecarboxaldehyde is a sole detectable by-product
?
additional information
additional information
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ferricyanide is highly efficient towards TSO II compared with TSO I
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?
additional information
additional information
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2,6-dichlorophenolindophenol preferred by TSO I, TSO II less active on L-tryptophan and almost inactive when alpha-amino group of tryptophan retained
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?
additional information
additional information
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dehydrogenase component abstracts electrons from the substrate and transfers them to oxidation-reduction dyes (e.g. potassium ferricyanide, 2,6-dichlorophenolindophenol) but not to molecular oxygen, the oxidase component transfers electrons from the former component to oxygen
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?
additional information
additional information
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overview: specificity
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?
additional information
additional information
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overview: specificity
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?
additional information
additional information
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substrate: tryptophan containing di- and oligopeptides
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?
additional information
additional information
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substrates: tryptophan residues in human alpha- and beta-globins
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?
additional information
additional information
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overview: specificity
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?
additional information
additional information
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substrate: tryptophan containing di- and oligopeptides
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?
