Ligand L-tryptophan

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Basic Ligand Information

Molecular Structure
Picture of L-tryptophan (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C11H12N2O2
L-tryptophan
QIVBCDIJIAJPQS-VIFPVBQESA-N
Synonyms:
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid, L-Trp, Trp, tryptophan

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (55 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-tryptophan + O2 = ? + H2O2
show the reaction diagram
-
L-tryptophan + O2 = N-formyl-L-kynurenine
show the reaction diagram
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L-tryptophan + O2 = formylkynurenine
show the reaction diagram
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L-tryptophan + O2 = 3-indoleglycolaldehyde + CO2 + NH3
show the reaction diagram
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L-tryptophan + FADH2 + chloride + O2 + H+ = 6-chloro-L-tryptophan + FAD + 2 H2O
show the reaction diagram
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L-tryptophan + O2 = 2-imino-3-(indol-3-yl)propanoate + H2O2
show the reaction diagram
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S-adenosyl-L-methionine + L-tryptophan = S-adenosyl-L-homocysteine + L-2-methyltryptophan
show the reaction diagram
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
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L-tryptophan + 2-oxoglutarate = L-glutamate + 3-indole-2-oxopropanoate
show the reaction diagram
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L-tryptophan + phenylpyruvate = 3-indole-2-oxopropanoate + L-phenylalanine
show the reaction diagram
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
show the reaction diagram
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L-tryptophan = tryptamine + CO2
show the reaction diagram
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Tryptophan = ?
show the reaction diagram
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L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
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L-tryptophan = 3-indoleacrylate + ammonia
show the reaction diagram
-
ATP + H2O + tryptophan/out = ADP + phosphate + tryptophan/in
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(indol-3-yl)pyruvate + NH3 + NADH + H+ = L-tryptophan + NAD+ + H2O
show the reaction diagram
-
-
L-tryptophanamide + H2O = L-tryptophan + NH3
show the reaction diagram
-
L-serine + indole = L-tryptophan + H2O
show the reaction diagram
-
-
ATP + H2O + tryptophan/out = ADP + phosphate + tryptophan/in
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (277 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-tryptophan + O2 = ?
show the reaction diagram
-
L-tryptophan + O2 = ? + H2O2
show the reaction diagram
-
Trp + H2O2 = ?
show the reaction diagram
-
L-tryptophan + O2 = N-formyl-L-kynurenine
show the reaction diagram
-
L-tryptophan + O2 = 3-(1H-indol-3-yl)-2-oxopropanoic acid + NH3
show the reaction diagram
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L-Trp + O2 = ? + CO2 + H2O
show the reaction diagram
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L-tryptophan + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (E)-indol-3-ylacetaldoxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
show the reaction diagram
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L-tryptophan + FADH2 + Cl- + O2 + H+ = 6-chloro-L-tryptophan + FAD + 2 H2O
show the reaction diagram
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L-tryptophan + O2 = alpha,beta-didehydrotryptophan + H2O2
show the reaction diagram
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L-tryptophan + H2O + NAD+ = 3-(1H-indol-3-yl)-2-oxopropanoate + NH3 + NADH
show the reaction diagram
-
L-tryptophan + H2O + 2 cytochrome b = 3-(1H-indol-3-yl)-2-oxopropanoic acid + NH3 + 2 reduced cytochrome b
show the reaction diagram
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S-adenosyl-L-methionine + L-tryptophan = S-adenosyl-L-homocysteine + L-2-methyltryptophan
show the reaction diagram
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L-Trp + acceptor protein = tRNA + L-Trp
show the reaction diagram
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
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2-oxosuccinamic acid + L-tryptophan = L-asparagine + 3-indole-2-oxopropanoate
show the reaction diagram
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
show the reaction diagram
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
show the reaction diagram
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
show the reaction diagram
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tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine
show the reaction diagram
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tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine
show the reaction diagram
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L-tryptophan + pyruvate = indolepyruvate + L-alanine
show the reaction diagram
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2-oxo-4-methylthiobutanoate + L-tryptophan = L-methionine + 3-(1H-indol-3-yl)-2-oxopropanoate
show the reaction diagram
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L-tryptophan + 2-oxoglutarate = 3-indole-2-oxopropanoate + L-glutamate
show the reaction diagram
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L-tryptophan + pyruvate = indole-3-pyruvate + L-alanine
show the reaction diagram
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benzyloxycarbonyl-Glu-methyl ester + L-tryptophan = benzyloxycarbonyl-Glu-Trp + methanol
show the reaction diagram
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L-tryptophan = tryptamine + CO2
show the reaction diagram
-
L-tryptophan + O2 + H2O = ?
show the reaction diagram
-
L-tryptophan = indole-acetic acid + CO2
show the reaction diagram
-
L-tryptophan + H2O = indole + pyruvate + NH3
show the reaction diagram
-
L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
-
L-tryptophan + D-glyceraldehyde 3-phosphate + H2O = indole-3-glycerol phosphate + L-serine
show the reaction diagram
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L-Trp = ?
show the reaction diagram
-
L-tryptophan = 3-indoleacrylate + ammonia
show the reaction diagram
-
L-tryptophan + H2O = ?
show the reaction diagram
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ATP + L-tryptophan + tRNAPhe = AMP + diphosphate + L-tryptophanyl-tRNAPhe
show the reaction diagram
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ATP + L-arginine + tryptophan = ? + AMP
show the reaction diagram
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ATP + L-asparagine + L-tryptophan = ADP + phosphate + L-asparaginyl-L-tryptophan
show the reaction diagram
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2 ATP + 2 L-Val + L-Trp = 2 ADP + 2 phosphate + L-Val-L-Val-L-Trp
show the reaction diagram
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ATP + H2O + tryptophan/out = ADP + phosphate + tryptophan/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (136 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(indol-3-yl)pyruvate + NH3 + NADH + H+ = L-tryptophan + NAD+ + H2O
show the reaction diagram
-
-
indole-3-pyruvate + NH3 + NADH = L-Trp + NADH + H2O
show the reaction diagram
-
-
5'-phospho-pyridoxyl-L-tryptophan + H2O + O2 = pyridoxal 5'-phosphate + L-tryptophan + H2O2
show the reaction diagram
-
alpha-N-methyl-L-tryptophan + O2 + H2O = L-tryptophan + formaldehyde + H2O2
show the reaction diagram
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5-L-glutamyl-L-Trp + Gly-Gly = L-Trp + 5-L-glutamyl-Gly-Gly
show the reaction diagram
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L-Trp + acceptor protein = tRNA + L-Trp
show the reaction diagram
-
-
indolepyruvate + L-aspartate = oxaloaspartate + L-tryptophan
show the reaction diagram
-
-
indolepyruvate + L-aspartate = L-tryptophan + oxaloacetate
show the reaction diagram
-
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3-indole-2-oxopropanoate + L-glutamate = L-tryptophan + 2-oxoglutarate
show the reaction diagram
-
-
L-Trp-7-amido-4-methylcoumarin + H2O = 7-amino-4-methylcoumarin + L-Trp
show the reaction diagram
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Trp-Leu + H2O = Trp + Leu
show the reaction diagram
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L-Trp-7-amido-4-methylcoumarin + H2O = 7-amino-4-methylcoumarin + L-Trp
show the reaction diagram
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Pro-Trp + H2O = Pro + Trp
show the reaction diagram
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N-acetyl-L-Trp + H2O = L-Trp + acetate
show the reaction diagram
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endothelin I + H2O = endothelin(1-20) + Trp
show the reaction diagram
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N-carbobenzoxy-Ala-Ala-Trp + H2O = N-carbobenzoxy-Ala-Ala + Trp
show the reaction diagram
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N-carboxybenzoyl-Ala-Trp + H2O = N-carboxybenzoyl-Ala + L-tryptophan
show the reaction diagram
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pyroglutamyl-Trp + H2O = pyroglutamate + Trp
show the reaction diagram
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N-Formyl-Met-Trp + H2O = N-Formyl-Met + Trp
show the reaction diagram
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eggshell membrane + H2O = Val-Leu-Pro-Pro + (X)-Val-Pro-Pro + Trp + ?
show the reaction diagram
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L-tryptophan amide + H2O = L-tryptophan + NH3
show the reaction diagram
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N-acetyl-L-tryptophan + H2O = acetate + L-tryptophan
show the reaction diagram
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glutaryl-tryptophan + H2O = glutarate + tryptophan
show the reaction diagram
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L-serine + indole = L-tryptophan + H2O
show the reaction diagram
-
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ATP + H2O + tryptophan/out = ADP + phosphate + tryptophan/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (49 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2g subcutaneously
-
induces
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stimulates oxidation of substrate L-arginine. Tryptophan or a derivative thereof may bind in the enzyme's pterin site, participate in arginine oxidation, and become nitrated at the 4-position
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stimulates conversion of prostaglandin G1 to H1
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5 mM, 1.24fold activation
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2fold increase at 0.2 mM
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stimulatory effect
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activates
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2 mM, 84% increase in activity of heart KAT at pH 8.0
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activation from 5-20 mM
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up to 1.3fold activation
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Inhibitor in Enzyme-catalyzed Reactions (128 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition at low concentrations
-
80% inhibition at 1.6 mM
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complete inhibition at 0.05 mM, reversible by increasing I- concentration
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35% inhibition at 2 mM and 22% inhibition at 0.2 mM
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reductive amination of pyruvate, 10 mM, 29% inhibition
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strong inhibitor
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at 20 mM, 15% inhibition
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complete inhibition of saccharopine formation
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reversible and competitive inhibition
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64% activity left at 1.1 mM
-
about 30% inhibition
-
40.7% activity at 1 mM
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15.5% residual activity at 5 mM
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weak inhibition, binds at the active site via the two zinc ions displacing the metal ions, binding structure analysis
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non-competitive inhibition, Ki: 5.24 mM
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competitive inhibition, 10 mM
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competitive inhibitor
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weak
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product inhibition at physiologic concentrations
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strong inhibitor
-
4% cell growth, 25% viability of cells
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (180 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.00813
-
pH 7.2, 30°C
0.0013
-
pH 7.0, 22°C
0.66
-
-
0.202
-
pH 7.8, 30°C
3.7
-
pH 8.0, 25°C
0.36
-
pH 8.5, 30°C
990
-
pH 8.0, 25°C
0.014
-
pH 8.0, 25°C
0.0035
-
mutant enzyme N412G/T415G/S418C/S437F, at pH 7.6, temperature not specified in the publication

KM Value (392 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.808
-
pH 7.0, 22°C
0.0058
-
-
11
-
-
1.53
-
pH 7.8, 30°C
6
-
pH 8.0, 25°C
1.42
-
recombinant enzyme, in 10 mM phosphate buffer (pH 7.4), 50 mM pyridoxal 5'-phosphate, at 37°C
3.4
-
pH 8.0, 20°C
0.3
-
-
0.00004
-
pH and temperature not specified in the publication
1.4
-
mutant enzyme N412G/T415G/S418C/S437F, at pH 7.6, temperature not specified in the publication

Ki Value (29 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.5
-
non-competitive inhibition
0.3
-
competitive vs. iron
0.7
-
-
0.2
-
mixed inhibition
1.9
-
apparent value
5.24
-
non-competitive inhibition
7
-
pH 8.0, 30°C
0.05
-
mixed inhibition
12
-
pH and temperature not specified in the publication, in absence of Brij 35

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00225
-
at 25°C in 0.2 M sodium phosphate buffer, pH 7.0

References & Links