Ligand 3-methyl-2-oxopentanoate

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Basic Ligand Information

Molecular Structure
Picture of 3-methyl-2-oxopentanoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H10O3
3-methyl-2-oxopentanoate
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, 3-methyl-2-ketovalerate, 3-methyl-2-oxo-n-valerate, 3-methyl-2-oxo-pentanoate, 3-methyl-2-oxo-pentanoic acid, 3-methyl-2-oxopentanoic acid, 3-methyl-2-oxovalerate, 3-methyl-2-oxovaleric acid, 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-oxopentanoate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
alpha-keto-beta-methylvaleric acid + NADH = ?
show the reaction diagram
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3-methyl-2-oxopentanoate = CO2 + 2-methylbutanal
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-isoleucine + H2O + NAD+ = 2-oxo-3-methylpentanoate + NH3 + NADH + H+
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2,3-dihydroxy-3-methylvalerate = 3-methyl-2-oxovalerate + H2O
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Substrate in Enzyme-catalyzed Reactions (54 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
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3-methyl-2-oxopentanoate + NADH = 2-hydroxy-3-methylpentanoate + NAD+
show the reaction diagram
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3-methyl-2-oxopentanoate + NADH + H+ = 2-hydroxy-3-methylpentanoate + NAD+
show the reaction diagram
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2-keto-3-methylvalerate + CoA + oxidized ferredoxin = 2-methylbutanoyl-CoA + CO2 + reduced ferredoxin
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2-oxo-3-methylvalerate + NADPH + NH3 = L-isoleucine + NADP+ + H2O
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3-methyl-2-oxopentanoate + NH3 + NADH + H+ = L-isoleucine + H2O + NAD+
show the reaction diagram
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(3S,3R)-2-oxo-3-methylvaleric acid + NH3 + NADPH + H+ = D-isoleucine + H2O + NADP+
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2-oxo-3-methylvalerate + L-glutamate = 2-amino-3-methylpentanoate + 2-oxoglutarate
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L-glutamine + 3-methyl-2-oxo-pentanoate = 2-oxoglutaramate + L-3-methyl-norvaline
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3-methyl-2-oxopentanoic acid = ?
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Product in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-2-hydroxy-beta-methylvalerate + 2,6-dichlorophenolindophenol = 3-methyl-2-oxopentanoate + reduced 2,6-dichlorophenolindophenol
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L-alpha-hydroxy-beta-methylvalerate + O2 = 3-methyl-2-oxopentanoate + H2O2
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L-isoleucine + H2O + NAD+ = 2-oxo-3-methylvalerate + NH3 + NADH + H+
show the reaction diagram
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L-isoleucine + H2O + NAD+ = 3-methyl-2-oxopentanoate + NADH + NH3
show the reaction diagram
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D-Ile + H2O + O2 = 3-methyl-2-oxopentanoate + H2O2
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D-isoleucine + H2O + methylene blue = 3-methyl-2-oxopentanoate + NH3 + reduced methylene blue
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L-isoleucine + H2O + 2 cytochrome b = 3-methyl-2-oxo-pentanoate + NH3 + 2 reduced cytochrome b
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pyruvate + L-isoleucine = L-alanine + 3-methyl-2-oxopentanoate
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isoleucine + pyruvate = 3-methyl-2-oxopentanoate + alanine
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isoleucine + glyoxylate = 3-methyl-2-oxopentanoate + glycine
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L-isoleucine + 2-oxoglutarate = 3-methyl-2-oxopentanoate + L-glutamate
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L-isoleucine + indole-3-pyruvic acid = 3-methyl-2-oxopentanoate + L-tryptophan
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L-isoleucine + 2-oxoglutarate = 3-methyl-2-oxopentanoate + L-glutamate
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (11 results)

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

kcat Value (Turnover Number) (32 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
7.2
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25C, pH 10.4
0.28
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pH 7.5, 25C
3.5
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pH 7.5, 45C
0.92
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in 100 mM potassium phosphate buffer (pH 7.4), at 37C
11
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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 30C
16
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mutant enzyme T377L/A460Y, at pH 6.0 and 30C

KM Value (55 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.8
-
pH 7.5, 25C, recombinant enzyme
0.21
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pH 7.0, 37C
13
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25C, pH 10.4
5.9
-
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0.027
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pH 7.5, 25C
0.1483
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pH 7.5, 45C
3.1
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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 30C
1.2
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mutant enzyme T377L/A460Y, at pH 6.0 and 30C

References & Links

Links to other databases for 3-methyl-2-oxopentanoate

ChEBI
PubChem
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PubChem