Ligand 4-methyl-2-oxopentanoate

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Basic Ligand Information

Molecular Structure
Picture of 4-methyl-2-oxopentanoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H10O3
4-methyl-2-oxopentanoate
BKAJNAXTPSGJCU-UHFFFAOYSA-M
Synonyms:
2-ketoisocaproate, 2-ketoisohexanoate, 2-oxo-4-methyl-pentanoic acid, 2-oxo-4-methylpentanoate, 2-oxo-4-methylpentanoic acid, 2-oxo-4-methyl valerate, 2-oxo-4-methylvaleric acid, 2-oxo-iso-caproate, 2-oxo-isocaproate, 2-Oxo-isohexanoate, 2-oxoisocaproate, 2-oxoisocaproic acid, 2-Oxoisohexanoate, 4-methyl-2-oxo-pentanoate, 4-Methyl-2-oxo-pentanoic acid, 4-methyl-2-oxopentanoic acid, 4-methyl-2-oxovalerate, 4-methyl-2-oxovaleric acid, alpha-keto-isocaproate, alpha-Ketoisocaproate, alpha-ketoisocaproic acid, alpha-ketoleucine, ketoleucine, oxoisohexanoate


Show all pahtways known for Show all BRENDA pathways known for 4-methyl-2-oxopentanoate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
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L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (131 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-methyl-2-oxopentanoate + NADH = 2-hydroxy-4-methylpentanoate + NAD+
show the reaction diagram
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2-oxo-4-methylpentanoate + NAD(P)H = (2R)-2-hydroxy-4-methylpentanoate + NAD(P)+
show the reaction diagram
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2-oxoisocaproate + NADPH + H+ = 2-hydroxy-4-methylpentanoate + NADP+
show the reaction diagram
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4-methyl-2-oxopentanoate + CoA + NAD+ = 3-methyl-butanoyl-CoA + CO2 + NADH
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2-ketoisocaproate + CoA + oxidized ferredoxin = CO2 + reduced ferredoxin + isovaleryl-CoA
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4-methyl-2-oxopentanoate + NH3 + NADH = 2-amino-4-methylpentanoate + NAD+ + H2O
show the reaction diagram
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4-methyl-2-oxopentanoic acid + NH3 + NADPH + H+ = ?
show the reaction diagram
2-oxo-iso-caproate + NADPH + NH3 = L-norleucine + NADP+ + H2O
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2-oxoisohexanoate + NH3 + NADH + H+ = L-leucine + H2O + NAD+
show the reaction diagram
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2-oxo-4-methylvaleric acid + NH3 + NADPH + H+ = D-leucine + H2O + NADP+
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4-methyl-2-oxopentanoate + acetyl-CoA = ?
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L-aspartate + 2-oxoisocaproate = oxaloacetate + L-leucine
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L-alanine + 2-oxoisohexanoate = pyruvate + L-leucine
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L-asparagine + 2-oxoisohexanoate = 2-oxosuccinamate + 2-aminoisohexanoate
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beta-alanine + 2-oxoisohexanoate = malonic semialdehyde + L-isoleucine
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L-alanine + 2-oxoisocaproate = pyruvate + 2-aminoisocaproate
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L-leucine + 4-methyl-2-oxopentanoate = 4-methyl-2-oxopentanoate + L-leucine
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (161 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-isopropylmalate + NAD+ = 2-oxoisocaproate + CO2 + NADH + H+
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2-hydroxyisocaproate + NAD+ = 2-oxoisocaproate + NADH + H+
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(R)-2-hydroxy-4-methylpentanoate + NAD+ = 4-methyl-2-oxopentanoate + NADH + H+
show the reaction diagram
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(2R)-hydroxy-4-methylpentanoate + 2-oxo-butyrate = 2-oxo-4-methylpentanoate + (2R)-hydroxybutyrate
show the reaction diagram
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L-leucine + H2O + NAD+ = 4-methyl-2-oxopentanoate + NH3 + NADH
show the reaction diagram
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L-leucine + H2O + NAD+ = 2-oxoisocaproate + NADH + NH3
show the reaction diagram
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D-Leu + H2O + O2 = 4-methyl-2-oxopentanoate + H2O2
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D-leucine + oxidized acceptor + H2O = 4-methyl-2-oxopentanoate + NH3 + reduced acceptor
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L-leucine + H2O + 2 cytochrome b = 2-oxo-4-methylpentanoate + NH3 + 2 reduced cytochrome b
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D-leucine + oxidized 2,6-dichloroindophenol + H2O = 4-methyl-2-oxopentanoate + NH3 + reduced 2,6-dichloroindophenol
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pyruvate + L-leucine = alanine + 4-methyl-2-oxopentanoate
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2-oxosuccinamic acid + L-leucine = L-asparagine + 4-methyl-2-oxopentanoate
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DL-ornithine + 2-oxoglutarate = L-glutamate + 4-methyl-2-oxopentanoate
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L-leucine + 2-oxoglutarate = 2-oxo-4-methylpentanoate + L-glutamate
show the reaction diagram
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D-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + D-glutamate
show the reaction diagram
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phenylpyruvate + DL-leucine = phenylalanine + 4-methyl-2-oxopentanoate
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L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
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L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
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L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
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L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
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L-leucine + phenylpyruvate = 4-methyl-2-oxopentanoate + L-phenylalanine
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L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
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D-leucine + 2-oxoadipate = 4-methyl-2-oxopentanoate + 2-aminoadipate
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L-leucine + pyruvate = 4-methyl-2-oxopentanoate + L-alanine
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2-oxo-4-methylthiobutanoate + L-leucine = L-methionine + 2-oxo-isocaproate
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L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
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L-leucine + indole-3-pyruvic acid = 2-oxo-4-methylpentanoate + L-tryptophan
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Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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Inhibitor in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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1 mM, 40.4% inhibition
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non-competitive inhibition at 5 mM, most active inhibitor of 2-keto acids, oxidation of 2-hydroxybutyrate most sensitive
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non competitive inhibition
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2-oxoglutarate dehydrogenase complex
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competitive inhibition
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competitive inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (11 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (68 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.33
-
wild-type enzyme
84
-
pH 7.0, temperature not specified in the publication
71.9
-
pH 9.5, 21C
71.9
-
-
5700
-
at pH 10.5 and 50C
17.8
-
pH 7.5, 45C
10
-
wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30C

KM Value (124 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
45
-
-
32.3
-
at pH 10.5 and 50C
0.03
-
with L-tryptophan, pH 8.0, 30C
2
-
pH 7.6, 37C
2.42
-
pH 7.0, 30C
0.9
-
wild type enzyme, in 100 mM KPO4 buffer (pH 7.0), 1 mM MgSO4, 0.5 mM thiamine diphosphate, at pH 7.0 and 30C

Ki Value (14 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
6.98
-
pH 8.0, 25C
2.71
-
pH 8.0, 25C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0749
-
at pH 7.5 and 25C

References & Links

Links to other databases for 4-methyl-2-oxopentanoate

ChEBI
PubChem
ChEBI
PubChem