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
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
alpha-keto-beta-methylvaleric acid + NADH = ?
-
show the reaction diagram
3-methyl-2-oxopentanoate = CO2 + 2-methylbutanal
-

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
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
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Substrate in Enzyme-catalyzed Reactions (54 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
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
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
2-oxo-3-methylvalerate + NADPH + NH3 = L-isoleucine + NADP+ + H2O
-
show the reaction diagram
3-methyl-2-oxopentanoate + NH3 + NADH + H+ = L-isoleucine + H2O + NAD+
-
show the reaction diagram
(3S,3R)-2-oxo-3-methylvaleric acid + NH3 + NADPH + H+ = D-isoleucine + H2O + NADP+
-
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 = ?
-

Product in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
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
D-isoleucine + H2O + methylene blue = 3-methyl-2-oxopentanoate + NH3 + reduced methylene blue
-
-
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
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Inhibitor in Enzyme-catalyzed Reactions (11 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
5 mM, 54.1% inhibition
-
2-oxoglutarate dehydrogenase complex
-
inhibition of the 2-oxoglutarate dehydrogenase enzyme complex in vivo and in situ, after 40 min 25% inhibition at 10 mM, 46% at 20 mM, after 80 min 58% inhibition at 10 mM, 80% at 20 mM, inhibition does not affect the mitochondrial membrane potential
-
inhibits KGDHC in PC-12 cells and does not alter mitochondrial membrane potential, but is associated with the release of cytochrome-c from mitochondria into the cytosol, reduction in basal cytosolic Ca2+, and diminishing endoplasmic reticulum calcium stores
-
severely inhibits KGDHC activity
-
competitive with respect to glycine, presence leads to a decrease of apparent Km for NAD with a concomitant decrease of Vmax
-
enzyme TUZN1299 is inhibited by keto acceptors in substrate inhibition, the maximum activity toward 4-methyl-2-oxovalerate and 3-methyl-2-oxovalerate in the reaction with L-alanine is achieved at a concentration of keto acids 1 mM, at 20 mM the specific activity of the enzyme decreases by 60% and 80%, respectively
-
measured in the forward reaction, concentrations higher than 1.0 mM inhibits the enzyme
-
more effective than 2-oxoisopentanoate
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (32 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 6.9, 85°C, under argon
25°C, pH 10.4
7.2
-
wild-type enzyme
280
-
mutant enzyme A113A/V291L
37
-
in 100 mM glycine-KCl-KOH buffer (pH 10), at 25°C
27.63
-
mutant enzyme A113A
235
-
pH 7.5, 25°C
0.28
-
pH 7.5, 45°C
3.5
-
pH 8.0, 37°C
12.15
-
SlBCAT4, pH not specified in the publication, 25°C
18.4
-
SlBCAT3, pH not specified in the publication, 25°C
23.6
-
SlBCAT2, pH not specified in the publication, 25°C
67.6
-
SlBCAT1, pH not specified in the publication, 25°C
16.3
-
pH not specified in the publication, 25°C
SlBCAT5, pH not specified in the publication, 25°C
23.6
-
SlBCAT6, pH not specified in the publication, 25°C
22.7
-
pH 8.0, 37°C
pH 8.0, 25°C
0.07
-
half transamination reaction, pH 8.0, 90°C
360
-
in 100 mM potassium phosphate buffer (pH 7.4), at 37°C
0.92
-
recombinant enzyme, pH 10.0, 40°C, with (R)-alpha-methylbenzylamine
0.15
-
pH 10.0, 40°C
0.15
-
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
11
-
mutant enzyme T377L/A460Y, at pH 6.0 and 30°C
16
-
-
19.75
-
pH and temperature not specified in the publication
pH 7.0, 55°C
0.5
-

KM Value (55 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 7.5, 25°C, recombinant enzyme
3.8
-
pH 7.0, 37°C
0.21
-
pH 6.9, 85°C, under argon
25°C, pH 10.4
13
-
-
6.7
-
pH 8.8, 30°C
3.33
-
pH 10.4, temperature not specified in the publication
1.06
-
pH 10.4, 30°C
6.7
-
-
3.33
-
VDH2
1.06
-
wild-type enzyme
3.8
-
mutant enzyme A113A
9.4
-
in 100 mM glycine-KCl-KOH buffer (pH 10), at 25°C
0.38
-
mutant enzyme A113A/V291L
69
-
pH 7.5, 25°C
0.027
-
pH 7.5, 45°C
0.1483
-
pH 8.3, 337°C
1.08
-
pH 8.0, 37°C
0.99
-
pH 8.4, 30°C
0.2
-
pH not specified in the publication, 25°C
SlBCAT1, pH not specified in the publication, 25°C
11.65
-
SlBCAT2, pH not specified in the publication, 25°C
12.4
-
SlBCAT3, pH not specified in the publication, 25°C
0.19
-
SlBCAT4, pH not specified in the publication, 25°C
0.14
-
SlBCAT5, pH not specified in the publication, 25°C
0.19
-
SlBCAT6, pH not specified in the publication, 25°C
0.16
-
pH 8.3, 25°C
0.07
-
pH 8.0, 37°C
pH 7.5, 25°C
0.21
-
half transamination reaction, pH 8.0, 90°C
0.034
-
recombinant enzyme, pH 10.0, 40°C, with (R)-alpha-methylbenzylamine
0.55
-
pH 10.0, 40°C
0.55
-
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
3.1
-
mutant enzyme T377L/A460Y, at pH 6.0 and 30°C
1.2
-
pH 7.0, 55°C
0.1
-
-
20.25
-
25°C, pH 7.2
0.87
-

References & Links

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

ChEBI
PubChem
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PubChem