Ligand 3-methyl-2-oxovaleric acid

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of 3-methyl-2-oxovaleric acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H10O3
3-methyl-2-oxovaleric acid
JVQYSWDUAOAHFM-UHFFFAOYSA-N
Synonyms:
(3S,3R)-2-oxo-3-methylvaleric acid, (R,S)-2-oxo-3-methylpentanoate, (R,S)-3-methyl-2-oxopentanoate, 2-keto-3-methyl-valerate, 2-keto-3-methylvalerate, 2-keto-beta-methylvalerate, 2-oxo-3-methyl-n-valeric acid, 2-oxo-3-methyl-valerate, 2-oxo-3-methylpentanoate, 2-oxo-3-methylvalerate, 2-oxo-beta-methyl-n-valerate, 2-oxo-beta-methylvalerate, 2-Oxoisohexanoate, 3-methyl-2-ketovalerate, 3-methyl-2-oxo-n-valerate, 3-methyl-2-oxo-pentanoate, 3-methyl-2-oxo-pentanoic acid, 3-methyl-2-oxopentanoate, 3-methyl-2-oxopentanoic acid, 3-methyl-2-oxovalerate, alpha-keto-beta-methyl-pentanoic acid, alpha-keto-beta-methylvalerate, alpha-keto-beta-methylvaleric acid, alpha-keto beta-methylvalerate, alpha-ketomethylvalerate, DL-2-oxo-3-methyl-n-pentanoate, DL-2-oxo-3-methylpentanoate, DL-3-methyl-2-oxopentanoate, DL-alpha-keto-beta-methyl-n-valerate, KMV


Show all pahtways known for Show all BRENDA pathways known for 3-methyl-2-oxovaleric 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
alpha-keto-beta-methylvaleric acid + NADH = ?
show the reaction diagram
-
3-methyl-2-oxopentanoate = CO2 + 2-methylbutanal
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-isoleucine + H2O + NAD+ = 2-oxo-3-methylpentanoate + NH3 + NADH + H+
show the reaction diagram
-
-
2,3-dihydroxy-3-methylvalerate = 3-methyl-2-oxovalerate + H2O
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (79 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-methyl-2-oxo-n-valerate + NADPH = 2-hydroxy-3-methyl-n-valerate + NADP+
show the reaction diagram
-
3-methyl-2-oxopentanoate + NADH = 2-hydroxy-3-methylpentanoate + NAD+
show the reaction diagram
-
2-oxo-3-methylvalerate + NADPH + H+ = 2-D-hydroxy-3-methylvalerate + NADP+
show the reaction diagram
-
3-methyl-2-oxopentanoate + NADH + H+ = 2-hydroxy-3-methylpentanoate + NAD+
show the reaction diagram
-
2-keto-3-methylvalerate + CoA + oxidized ferredoxin = 2-methylbutanoyl-CoA + CO2 + reduced ferredoxin
show the reaction diagram
-
3-methyl-2-oxopentanoic acid + NH3 + NADPH + H+ = D-isoleucine + NADP+
show the reaction diagram
-
2-oxo-3-methylvalerate + NADPH + NH3 = L-isoleucine + NADP+ + H2O
show the reaction diagram
-
2-oxoisohexanoate + NH3 + NADH = L-Leu + NAD+ + H2O
show the reaction diagram
-
(3S,3R)-2-oxo-3-methylvaleric acid + NH3 + NADPH + H+ = D-isoleucine + H2O + NADP+
show the reaction diagram
-
L-alanine + 2-oxoisohexanoate = pyruvate + L-leucine
show the reaction diagram
-
L-asparagine + 2-oxoisohexanoate = 2-oxosuccinamate + 2-aminoisohexanoate
show the reaction diagram
-
beta-alanine + 2-oxoisohexanoate = malonic semialdehyde + L-isoleucine
show the reaction diagram
-
2-oxo-3-methylvalerate + L-glutamate = 2-amino-3-methylpentanoate + 2-oxoglutarate
show the reaction diagram
-
L-glutamine + 3-methyl-2-oxo-pentanoate = 2-oxoglutaramate + L-3-methyl-norvaline
show the reaction diagram
-
3-methyl-2-oxopentanoic acid = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (126 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(2R,3S)-3-isopropylmalate + thionicotinamide NAD+ = 2-oxoisohexanoate + thionicotinamideNADH + CO2
show the reaction diagram
-
-
L-2-hydroxy-beta-methylvalerate + 2,6-dichlorophenolindophenol = 3-methyl-2-oxopentanoate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
L-alpha-hydroxy-beta-methylvalerate + O2 = 3-methyl-2-oxopentanoate + H2O2
show the reaction diagram
-
-
L-isoleucine + H2O + NAD+ = 2-oxo-3-methylvalerate + NH3 + NADH + H+
show the reaction diagram
-
-
L-isoleucine + H2O + NAD+ = 3-methyl-2-oxopentanoate + NADH + NH3
show the reaction diagram
-
D-Ile + H2O + O2 = 3-methyl-2-oxopentanoate + H2O2
show the reaction diagram
-
-
L-isoleucine + H2O + 2 cytochrome b = 3-methyl-2-oxo-pentanoate + NH3 + 2 reduced cytochrome b
show the reaction diagram
-
-
pyruvate + L-isoleucine = L-alanine + 3-methyl-2-oxopentanoate
show the reaction diagram
-
isoleucine + pyruvate = 3-methyl-2-oxopentanoate + alanine
show the reaction diagram
-
isoleucine + glyoxylate = 3-methyl-2-oxopentanoate + glycine
show the reaction diagram
-
-
L-isoleucine + 2-oxoglutarate = 3-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
-
L-isoleucine + indole-3-pyruvic acid = 3-methyl-2-oxopentanoate + L-tryptophan
show the reaction diagram
-
-
L-isoleucine + 2-oxoglutarate = 3-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, 54.1% inhibition
-
competitive with respect to glycine, presence leads to a decrease of apparent Km for NAD with a concomitant decrease of Vmax
-

3D Structure of Enzyme-Ligand-Complex (PDB) (8 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (35 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
71.9
-
pH 9.5, 21°C
0.28
-
pH 7.5, 25°C
3.5
-
pH 7.5, 45°C
0.92
-
in 100 mM potassium phosphate buffer (pH 7.4), at 37°C
11
-
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
16
-
mutant enzyme T377L/A460Y, at pH 6.0 and 30°C

KM Value (76 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.8
-
pH 7.5, 25°C, recombinant enzyme
0.21
-
pH 7.0, 37°C
5.9
-
-
0.027
-
pH 7.5, 25°C
0.03
-
with L-tryptophan, pH 8.0, 30°C
0.1483
-
pH 7.5, 45°C
3.1
-
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
1.2
-
mutant enzyme T377L/A460Y, at pH 6.0 and 30°C

References & Links

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

ChEBI
PubChem
ChEBI
PubChem