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EC Tree
IUBMB Comments Requires heme. The enzyme from Chromobacterium violaceum is specific for tryptophan derivatives possessing its carboxyl group free or as an amide or ester, and an unsubstituted indole ring. Also catalyses the alpha,beta dehydrogenation of L-tryptophan side chains in peptides. The product of the reaction can hydrolyse spontaneously to form (indol-3-yl)pyruvate.
The enzyme appears in viruses and cellular organisms
Synonyms
EC 1.4.3.17, L-tryptophan 2',3'-oxidase, L-tryptophan alpha,beta-dehydrogenase, LTO, tryptophan side chain oxidase II,
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EC 1.4.3.17
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formerly
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L-tryptophan 2',3'-oxidase
L-tryptophan alpha,beta-dehydrogenase
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tryptophan side chain oxidase II
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L-tryptophan 2',3'-oxidase
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L-tryptophan 2',3'-oxidase
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L-tryptophan 2',3'-oxidase
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LTO
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L-tryptophan + O2 = alpha,beta-didehydrotryptophan + H2O2
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L-tryptophan:oxygen alpha,beta-oxidoreductase
Requires heme. The enzyme from Chromobacterium violaceum is specific for tryptophan derivatives possessing its carboxyl group free or as an amide or ester, and an unsubstituted indole ring. Also catalyses the alpha,beta dehydrogenation of L-tryptophan side chains in peptides. The product of the reaction can hydrolyse spontaneously to form (indol-3-yl)pyruvate.
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adrenocorticotropic hormone + O2
? + H2O2
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?
calcium-dependent lipopeptide antibiotic + O2
? + H2O2
indole-3-propionate + O2
? + H2O2
L-tryptophan + O2
alpha,beta-didehydrotryptophan + H2O2
L-tryptophanamide + O2
alpha,beta-didehydrotryptophanamide + H2O2
luteinizing hormone-releasing hormone + O2
? + H2O2
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?
N-acetyl-L-tryptophan + O2
N-acetyl-alpha,beta-didehydrotryptophan + H2O2
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O2
pentagastrin + O2
N-[(2E)-2-{[N-(tert-butoxycarbonyl)-beta-alanyl]amino}-3-(1H-indol-3-yl)prop-2-enoyl]-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide + H2O2
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?
tryptophan No.14 of alpha-globin + O2
alpha,beta-dehydrotryptophan + H2O2
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?
tryptophan No.15 of beta-globin + O2
alpha,beta-dehydrotryptophan + H2O2
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?
calcium-dependent lipopeptide antibiotic + O2
? + H2O2
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?
calcium-dependent lipopeptide antibiotic + O2
? + H2O2
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?
indole-3-propionate + O2
? + H2O2
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?
indole-3-propionate + O2
? + H2O2
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?
L-tryptophan + O2
alpha,beta-didehydrotryptophan + H2O2
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?
L-tryptophan + O2
alpha,beta-didehydrotryptophan + H2O2
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?
L-tryptophanamide + O2
alpha,beta-didehydrotryptophanamide + H2O2
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?
L-tryptophanamide + O2
alpha,beta-didehydrotryptophanamide + H2O2
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?
N-acetyl-L-tryptophan + O2
N-acetyl-alpha,beta-didehydrotryptophan + H2O2
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?
N-acetyl-L-tryptophan + O2
N-acetyl-alpha,beta-didehydrotryptophan + H2O2
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O2
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O2
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O2
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?
N-acetyl-L-tryptophanamide + O2
N-acetyl-alpha,beta-didehydrotryptophanamide + H2O2
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?
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additional information
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NAD+, NADP+, FAD, or FMN show no effect on the activity
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MgCl2
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10 mM, residual activity 103%
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Sodium dodecyl sulfate
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no modification with 0.4% SDS
Urea
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no modification with 8 M urea
5-hydroxy-L-tryptophan
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competitive inhibition, Ki: 0.037 mM
5-hydroxy-L-tryptophan
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D-tryptophan
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competitive inhibition, Ki: 0.0066 mM
methyl-3-indole
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competitive inhibition, Ki: 0.0013 mM
tryptamine
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competitive inhibition, Ki: 0.0054 mMl
additional information
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no inhibition with L-histidine, N-acetyl-L-phenylalaninamide and N-acetyl-L-tyrosinamide
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additional information
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no inhibition with L-histidine, N-acetyl-L-phenylalaninamide and N-acetyl-L-tyrosinamide
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0.93
adrenocorticotropic hormone
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dehydrogenation of the tryptophanyl side chain
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0.02
indole-3-propionate
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0.0091
L-Tryptophanamide
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0.071
Luteinizing hormone-releasing hormone
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dehydrogenation of the tryptophanyl side chain
0.0791
N-acetyl-L-tryptophan
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0.0195
N-Acetyl-L-tryptophanamide
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0.026
pentagastrin
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dehydrogenation of the tryptophanyl side chain
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0.283
adrenocorticotropic hormone
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dehydrogenation of the tryptophanyl side chain
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0.785
indole-3-propionate
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0.593
L-Tryptophanamide
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0.333
Luteinizing hormone-releasing hormone
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dehydrogenation of the tryptophanyl side chain
0.79
N-acetyl-L-tryptophan
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0.753
N-Acetyl-L-tryptophanamide
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0.533
pentagastrin
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dehydrogenation of the tryptophanyl side chain
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0.037
5-hydroxy-L-tryptophan
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0.0013
methyl-3-indole
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0.02
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substrate tryptophanamide
0.07
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substrate tryptophan-leucine
0.31
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substrate tryptophan
0.74
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substrate leucin-tryptophan-leucin
1.08
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substrate indolepropionic acid
1.42
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substrate N-acetyltryptophanamide
1.82
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substrate N-acetyltryptophan
2.32
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substrate leucin-tryptophan
30.3
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after purification
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strain ATCC12472
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brenda
strain ATCC12472
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brenda
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brenda
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brenda
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14000
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alpha, 4 * 14000 + beta 4 * 74000, organized in an alpha4,beta4 manner, heterooligomeric structure, one heme molecule per alpha,beta protomer, SDS-PAGE
74000
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alpha, 4 * 14000 + beta 4 * 74000, organized in an alpha4,beta4 manner, heterooligomeric structure, one heme molecule per alpha,beta protomer, SDS-PAGE
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octamer
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alpha, 4 * 14000 + beta 4 * 74000, organized in an alpha4,beta4 manner, heterooligomeric structure, one heme molecule per alpha,beta protomer, SDS-PAGE
octamer
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alpha, 4 * 14000 + beta 4 * 74000, organized in an alpha4,beta4 manner, heterooligomeric structure, one heme molecule per alpha,beta protomer, SDS-PAGE
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7
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after dilution in 0.1 M bis-Tris buffer
639382
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active with 0.2 M dithiothreitol, 1% SDS, or 4.5 M urea
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-80°C, for several months and for 24-48 h at room temperature in the absence of any additives
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cell disruption with Eaton press, ultracentrifugation, ammonium sulfate precipitation, DEAE-column, concentration using centrifugal microcentrators, gel filtration, purified 108fold, yield 33.8%
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gel filtration, phosphocellulose column chromatography, SDS-PAGE
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Takai, K.; Sasai, Y.; Morimoto, H.; Yamazaki, H.; Yoshii, H.; Inoue, S.
Enzymatic dehydrogenation of tryptophan residues of human globins by tryptophan side chain oxidase II
J. Biol. Chem.
259
4452-4457
1984
Pseudomonas sp.
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Ito, S.; Takai, K.; Tokuyama, T.; Hayaishi, O.
Enzymatic modification of tryptophan residues by tryptophan side chain oxidase I and II from Pseudomonas
J. Biol. Chem.
256
7834-7843
1981
Pseudomonas sp.
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Genet, R.; Benetti, P.H.; Hammadi, A.; Menez, A.
L-tryptophan 2',3'-oxidase from Chromobacterium violaceum
J. Biol. Chem.
270
23540-23545
1995
Chromobacterium violaceum, Chromobacterium violaceum ATCC 12472
brenda
Genet, R.; Donoyelle, C.; Menez, A.
Purification and partial characterization of an amino acid alpha,beta-dehydrogenase, L-tryptophan 2',3'-oxidase from Chromobacterium violaceum
J. Biol. Chem.
269
18177-18184
1994
Chromobacterium violaceum, Chromobacterium violaceum ATCC 12472
brenda
Amir-Heidari, B.; Thirlway, J.; Micklefield, J.
Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics
Org. Lett.
9
1513-1516
2007
Streptomyces coelicolor, Streptomyces coelicolor WH101.10
brenda
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