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BRENDA support

Ligand 3-methyl-2-oxobutanoic acid

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Basic Ligand Information

Molecular Structure
Picture of 3-methyl-2-oxobutanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H8O3
3-methyl-2-oxobutanoic acid
QHKABHOOEWYVLI-UHFFFAOYSA-N
Synonyms:
2-ketoisopentanoate, 2-ketoisovalerate, 2-oxo-3-methylbutanoate, 2-oxo-3-methylbutanoic acid, 2-oxo-3-methylbutyric acid, 2-oxo-iso-valerate, 2-oxo-isopentanoate, 2-oxo-isovalerate, 2-oxoiso-valerate, 2-oxoisopentanoate, 2-oxoisopentanoic acid, 2-oxoisovalerate, 2-oxoisovaleric acid, 2-oxovaline, 3,3-dimethyl-2-oxo-propionate, 3-methyl-2-ketobutyrate, 3-methyl-2-oxo-butanoate, 3-methyl-2-oxobutanoate, 3-methyl-2-oxobutyrate, 3-methyl-2-oxobutyric acid, alpha-ketoisovaleric acid, ketovaline
Pathway Source
Pathways
BRENDA
alanine metabolism, leucine metabolism, pantothenate biosynthesis, valine metabolism
KEGG
2-Oxocarboxylic acid metabolism, Biosynthesis of amino acids, Biosynthesis of cofactors, Biosynthesis of secondary metabolites, Glucosinolate biosynthesis more
MetaCyc
2-oxoisovalerate decarboxylation to isobutanoyl-CoA, 3-methylbutanol biosynthesis (engineered), butanol and isobutanol biosynthesis (engineered), even iso-branched-chain fatty acid biosynthesis, hectochlorin biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for 3-methyl-2-oxobutanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxoisovalerate = isobutyraldehyde + CO2
show the reaction diagram
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3-methyl-2-oxobutyrate + L-glutamate = L-valine + 2-oxoglutarate
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (13 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(R)-3,3-dimethylmalate + NAD+ = 3-methyl-2-oxobutanoate + CO2 + NADH
show the reaction diagram
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DL-2-hydroxyisovalerate + O2 = 2-oxoisovalerate + H2O2
show the reaction diagram
-
L-valine + NAD(P)+ + H2O = 2-oxoisovalerate + NH3 + NAD(P)H
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (140 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-ketoisopentanoate + NAD(P)H = 2-hydroxyisopentanoate + NAD(P)+
show the reaction diagram
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2-oxoisovalerate + NADPH = 2-hydroxyvalerate + NADP+
show the reaction diagram
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3-methyl-2-oxobutanoate + NADH = 2-hydroxy-3-methylbutanoate + NAD+
show the reaction diagram
-
2-oxoisovalerate + NADH + H+ = 2-hydroxyisovalerate + NAD+
show the reaction diagram
-
2-oxoisovalerate + NADH + H+ = ? + NAD+
show the reaction diagram
-
2-ketoisovalerate + NADPH + H+ = ?
show the reaction diagram
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2-oxoisovalerate + CoA + NAD+ = isobutanoyl-CoA + CO2 + NADH
show the reaction diagram
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2-oxoisovalerate + NAD+ + CoA-SH = ?
show the reaction diagram
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2-oxoisovalerate + oxidized 2,6-dichlorophenolindophenol = 2-methylpropanal + CO2 + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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3-methyl-2-oxobutanoate + H2O + oxidized methyl viologen = S-(2-methylpropanoyl)-CoA + reduced methyl viologen + H+
show the reaction diagram
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2-oxo-3-methylbutanoate + NH3 + NADH = L-Val + NAD+ + H2O
show the reaction diagram
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2-oxo-iso-valerate + NADPH + NH3 = L-leucine + NADP+ + H2O
show the reaction diagram
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2-oxo-3-methylbutyric acid + NH3 + NADPH + H+ = D-valine + H2O + NADP+
show the reaction diagram
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2-oxoisovalerate = isobutyraldehyde + CO2
show the reaction diagram
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2-oxoisovalerate + acetyl-CoA = isopropylmalate + CoA
show the reaction diagram
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acetyl-CoA + 2-oxoisovalerate + H2O = ?
show the reaction diagram
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acetyl-CoA + H2O + 2-ketoisovalerate = ?
show the reaction diagram
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L-alanine + 2-oxoisopentanoate = pyruvate + L-valine
show the reaction diagram
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beta-alanine + 2-oxoisopentanoate = malonic semialdehyde + L-valine
show the reaction diagram
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D-alanine + 2-oxoisovalerate = pyruvate + D-valine
show the reaction diagram
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histidine + 2-oxoisovalerate = imidazol-5-yl-pyruvate + L-valine
show the reaction diagram
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2-oxoisovalerate + L-glutamate = L-valine + 2-oxoglutarate
show the reaction diagram
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L-glutamine + 2-oxoisovalerate = 2-oxoglutaramate + L-valine
show the reaction diagram
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(R)-alpha-methylbenzylamine + 3-methyl-2-oxobutyrate = acetophenone + L-valine
show the reaction diagram
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3-methyl-2-oxobutanoic acid = ?
show the reaction diagram
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2-oxoisovalerate = ?
show the reaction diagram
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2-Oxo-3-methylbutanoate + formaldehyde = 2-Dehydropantoate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (85 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-hydroxyisovalerate + NAD+ = 2-oxoisovalerate + NADH + H+
show the reaction diagram
-
(R)-3,3-dimethylmalate + NAD+ = 3-methyl-2-oxobutanoate + CO2 + NADH
show the reaction diagram
-
(R,S)-2-hydroxyisovalerate + acceptor = 2-oxo-isovalerate + reduced acceptor
show the reaction diagram
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isobutyryl-CoA + CO2 + reduced benzyl viologen = 2-oxoisopentanoate + CoA + benzyl viologen
show the reaction diagram
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D-valine + oxidized 2,6-dichloroindophenol + H2O = 2-oxoisopentanoate + NH3 + reduced 2,6-dichloroindophenol
show the reaction diagram
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S-adenosyl-L-methionine + 2-oxobutyrate = S-adenosyl-L-homocysteine + 3-methyl-2-oxobutyrate
show the reaction diagram
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pyruvate + L-valine = L-alanine + 3-methyl-2-oxobutanoate
show the reaction diagram
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phenylpyruvate + DL-valine = phenylalanine + 3-methyl-2-oxobutanoate
show the reaction diagram
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L-valine + (S)-3-methyl-2-oxopentanoate = 3-methyl-2-oxobutanoate + L-isoleucine
show the reaction diagram
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L-valine + glyoxylate = 3-methyl-2-oxobutanoate + glycine
show the reaction diagram
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valine + pyruvate = 3-methyl-2-oxobutanoate + alanine
show the reaction diagram
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L-valine + alpha-ketomethiobutyrate = 3-methyl-2-oxo-butanoate + L-methionine
show the reaction diagram
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valine + glyoxylate = 3-methyl-2-oxobutanoate + glycine
show the reaction diagram
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D-valine + 2-oxoadipate = 3-methyl-2-oxobutanoate + 2-aminoadipate
show the reaction diagram
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2-oxo-4-methylthiobutanoate + L-valine = L-methionine + 2-oxo-isovalerate
show the reaction diagram
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L-valine + indole-3-pyruvic acid = 3-methyl-2-oxobutanoate + L-tryptophan
show the reaction diagram
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L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
-

Inhibitor in Enzyme-catalyzed Reactions (16 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
10 mM, 43.1% inhibition
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0.01 M, 21% inhibition
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non-competitive inhibition at 5 mM
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2-oxoglutarate dehydrogenase complex
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competitive
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substrate inhibition
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65 mM, 50% loss of specific activity
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competitive
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transamination between glutamine and glyoxylate
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measured in the forward reaction, concentrations higher than 1.0 mM inhibits the enzyme

3D Structure of Enzyme-Ligand-Complex (PDB) (71 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (119 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.182
-
pH 8.0, 37°C
226
-
pH 9.5, 21°C
0.18
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at pH 8.0 and 32°C
2.1
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pH 7.5, 45°C
0.92
-
in 100 mM potassium phosphate buffer (pH 7.4), at 37°C
19
-
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
12
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mutant enzyme T377L/A460Y, at pH 6.0 and 30°C

KM Value (182 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
8.7
-
pH 7.5, 25°C, recombinant enzyme
0.065
-
pH 7.0, 30°C
6.91
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pH 8.0, 37°C, wild-type enzyme
1.27
-
pH 7.0, 30°C
1
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at pH 8.0 and 32°C
0.11
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with L-tryptophan, pH 8.0, 30°C
0.0133
-
pH 7.5, 45°C
8.5
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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
0.77
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mutant enzyme T377L/A460Y, at pH 6.0 and 30°C

References & Links

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Links to other databases for 3-methyl-2-oxobutanoic acid

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ChEBI
PubChem
ChEBI
PubChem