Ligand 4-methylthio-2-oxobutanoic acid

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Basic Ligand Information

Molecular Structure
Picture of 4-methylthio-2-oxobutanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H8O3S
4-methylthio-2-oxobutanoic acid
SXFSQZDSUWACKX-UHFFFAOYSA-N
Synonyms:
(4-methylsulfanyl)-2-oxobutanoate, 2-keto-4-methylthiobutyrate, 2-keto-4-methyl thiobutyrate, 2-keto-4-thiomethylbutyric acid, 2-keto-gamma-methylthiobutanoate, 2-ketomethylthiobutyrate, 2-oxo-4-(methylthio)butanoate, 2-oxo-4-methiolbutyrate, 2-oxo-4-methyl-thio-butyrate, 2-oxo-4-methyl-thiobutanoate, 2-oxo-4-methylmercaptobutyrate, 2-oxo-4-methylthiobutanoate, 2-oxo-4-methylthiobutanoic acid, 2-oxo-4-methylthiobutyrate, 2-oxo-4-methylthiobutyric acid, 2-oxo-4-thiomethylbutanoate, 2-oxo-gamma-methylthiobutanoate, 2-oxo-gamma-methylthiobutyrate, 2-oxo-methiolbutyrate, 2-oxomethylthiobutanoate, 2-oxomethylthiobutyrate, 2-oxomethylthiobutyric acid, 4-(methylsulfanyl)-2-oxobutanoate, 4-(methylsulfanyl)-2-oxobutanoic acid, 4-(methylthio)-2-oxobutanoate, 4-(methylthio)-2-oxobutanoic acid, 4-(methylthio)oxobutanoate, 4-methylsulfanyl-2-oxobutanaote, 4-methylsulfanyl-2-oxobutanoate, 4-methylsulfanyl-2-oxobutyrate, 4-methylsulfanyl-2-oxobutyric acid, 4-methylthio-2-ketobutyrate, 4-methylthio-2-oxo-butanoate, 4-methylthio-2-oxobutanoate, 4-methylthio-2-oxobutyrate, alpha-keto-gamma-methiobutyrate, alpha-keto-gamma-methiobutyric acid, alpha-keto-gamma-methiolbutyrate, alpha-keto-gamma-methylthiobutyrate, alpha-ketomethiobutyrate, alpha-oxo-gamma-methiol-butyric acid


Show all pahtways known for Show all BRENDA pathways known for 4-methylthio-2-oxobutanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxo-4-methylthiobutanoate + acetyl-CoA + H2O = 2-(2'-methylthio)ethylmalate + CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-methionine + pyruvate = 4-methylthio-2-oxobutanoate + L-alanine
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (90 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxomethylthiobutyrate + NADH + H+ = ? + NAD+
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4-methylthio-2-oxobutanoate + H2O2 = ?
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2-oxo-4-methyl-thio-butyrate + CoA + 2 methyl viologen = ?
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2-oxo-4-methylthiobutyrate + CoA + 2 methyl viologen = 3-methylthiopropanoyl-CoA + CO2 + 2 reduced methyl viologen + 2 H+
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4-methylthio-2-oxobutanoate + CoA + oxidized ferredoxin = 3-methylthio-2-oxopropanoyl-CoA + CO2 + reduced ferredoxin
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2-keto-4-methylthiobutyrate + CoA + oxidized ferredoxin = CO2 + reduced ferredoxin + 3-methylthiopropionyl-CoA
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2-oxo-4-methylthiobutanoate + NH3 + NADH = L-Met + NAD+ + H2O
show the reaction diagram
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5,10-methylenetetrahydrofolate + 2-oxo-4-methylthiobutyrate = tetrahydrofolate + ?
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acetyl-CoA + 4-methylthio-2-oxobutyrate + H2O = ?
show the reaction diagram
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L-asparagine + 4-methylsulfanyl-2-oxobutanoate = 2-oxosuccinamate + L-methionine
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L-tryptophan + 2-oxomethylthiobutanoate = (indol-3-yl)pyruvate + 2-aminomethylthiobutanoate
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L-alanine + 4-methylthio-2-oxobutyrate = pyruvate + L-methionine
show the reaction diagram
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L-phenylalanine + 2-oxo-4-methylthiobutyrate = phenylpyruvate + L-methionine
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L-kynurenine + 4-methylsulfanyl-2-oxobutanoate = 4-(2-aminophenyl)-2,4-dioxobutanoate + L-methionine
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S-(4-bromophenyl)-L-cysteine + 4-methylsulfanyl-2-oxobutanoate = S-(4-bromophenyl)-3-thiopyruvate + methionine
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4-methylthio-2-oxobutanoate = 3-methylthiopropanal + CO2
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4-methylthio-2-oxobutanoate = 3-(methylsulfanyl)propanal + CO2
show the reaction diagram
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alpha-keto-gamma-methiobutyric acid + L-aspartate = ?
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Product in Enzyme-catalyzed Reactions (85 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + O2 = 4-methylthio-2-ketobutyrate + formate + CO
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L-Met + O2 = 2-oxo-methiolbutyrate + NH3 + H2O2
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L-methionine + H2O + NAD+ = 4-(methylsulfanyl)-2-oxobutanoate + NH3 + NADH
show the reaction diagram
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L-methionine + H2O + NAD+ = (4-methylsulfanyl)-2-oxobutanoate + NH3 + NADH
show the reaction diagram
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L-methionine + H2O + NAD+ = 4-(methylthio)-2-oxobutanoic acid + NH3 + NADH
show the reaction diagram
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L-Met + H2O + NAD+ = 4-methylthio-2-oxobutyrate + NH3 + NADH
show the reaction diagram
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D-methionine + H2O + O2 = 4-(methylsulfanyl)-2-oxobutanoic acid + NH3 + H2O2
show the reaction diagram
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L-methionine + H2O + 2 cytochrome b = 4-methylsulfanyl-2-oxobutanoate + NH3 + 2 reduced cytochrome b
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L-methionine + 2-oxoglutarate = L-glutamate + 4-methylsulfanyl-2-oxobutyric acid
show the reaction diagram
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phenylpyruvate + DL-methionine = phenylalanine + 4-methylsulfanyl-2-oxobutanoate
show the reaction diagram
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
show the reaction diagram
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L-methionine + phenylpyruvate = 4-methylsulfanyl-2-oxobutanoate + L-phenylalanine
show the reaction diagram
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L-methionine + 2-oxoglutarate = 4-methylsulfanyl-2-oxobutanoate + L-glutamate
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L-methionine + glyoxylate = 4-methylsulfanyl-2-oxobutanoate + glycine
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D-methionine + 2-oxoadipate = 4-methylsulfanyl-2-oxobutanoate + 2-aminoadipate
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L-methionine + indole-3-pyruvic acid = 2-oxo-4-methylthiobutanoate + L-tryptophan
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1 mM, 10% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.667
-
pH 6.9, 85°C, under argon
0.12
-
isoform IPMS3, pH and temperature not specified in the publication
1.3
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at pH 8.0 and 32°C
620
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pH 8.0, 25°C
7.7
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wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30°C

KM Value (35 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.26
-
at pH 7.0 and 37°C
0.058
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pH 6.9, 85°C, under argon
0.734
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isoform IPMS3, pH and temperature not specified in the publication
0.35
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cosubstrate L-asparagine
3.2
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pH 8.4, 37ºC
0.33
-
37°C
0.64
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wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30°C

References & Links

Links to other databases for 4-methylthio-2-oxobutanoic acid

ChEBI
PubChem
ChEBI
PubChem