Ligand 2-Oxopentanoate

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Basic Ligand Information

Molecular Structure
Picture of 2-Oxopentanoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H8O3
2-Oxopentanoate
KDVFRMMRZOCFLS-UHFFFAOYSA-M
Synonyms:
2-ketopentanoate, 2-ketopentanoic acid, 2-Ketovalerate, 2-oxo-n-pentanoate, 2-oxo-pentanoate, 2-Oxo-valeric acid, 2-Oxopentanoic acid, 2-oxovalerate, 2-Oxovaleric acid, 2-oxpentanoate, 3-ethylpyruvate, alpha-keto-n-valerate, alpha-ketoisovalerate, alpha-ketovalerate
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + alpha-ketoisovalerate + H2O = alpha-isopropylmalate + CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
DL-2-hydroxyvalerate + O2 = 2-oxovalerate + H2O2
show the reaction diagram
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2,3-dihydroxyisovalerate = 2-oxovalerate + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (87 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxopentanoate + NADH + H+ = 2-hydroxypentanoate + NAD+
show the reaction diagram
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2-oxovalerate + NADH + H+ = 2-hydroxyvalerate + NAD+
show the reaction diagram
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alpha-ketoisovalerate + NADH = 2-hydroxyisovalerate + NAD+
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2-ketovalerate + NADPH + H+ = ?
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2-oxovalerate + CoA + NAD+ = ? + CO2 + NADH
show the reaction diagram
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2-oxovalerate + oxidized 2,6-dichlorophenolindophenol = butanal + CO2 + reduced 2,6-dichlorophenolindophenol
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2-oxopentanoate + NAD+ + CoA = butanoyl-CoA + CO2 + NADH
show the reaction diagram
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2-oxovalerate + H2O + methyl viologen = ?
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2-ketovalerate + CoA + benzyl viologen = butanoyl-CoA + CO2 + reduced benzyl viologen
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2-oxovalerate + NH3 + NADH + H+ = L-valine + H2O + NAD+
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2-oxopentanoate + NH3 + NADH = L-norvaline + NAD+ + H2O
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2-oxovalerate + H2O + NAD+ = L-norvaline + NH3 + NADH + H+
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L-Arg + 2-oxovalerate + NADH = ?
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L-Ala + 2-oxopentanoate + NADH = ?
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Gly + 2-oxopentanoate + NADH = ?
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Taurine + 2-oxopentanoate + NADH = ?
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L-lysine + alpha-ketovalerate + NADH = ?
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S-adenosyl-L-methionine + 2-oxovalerate = S-adenosyl-L-homocysteine + (3R)-methyl-2-oxovalerate
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acetyl-CoA + H2O + 2-ketovalerate = (R)-2-(n-propyl)-malate + CoA
show the reaction diagram
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L-alanine + 2-oxopentanoate = pyruvate + L-norvaline
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beta-alanine + 2-oxopentanoate = malonic semialdehyde + L-norvaline
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L-tryptophan + 2-oxopentanoate = 3-indole-2-oxopropanoate + norvaline
show the reaction diagram
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L-lysine + 2-oxopentanoate = 2-aminoadipate 6-semialdehyde + 2-aminopentanoate
show the reaction diagram
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histidine + 2-oxovalerate = imidazol-5-yl-pyruvate + L-norvaline
show the reaction diagram
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(R)-3-amino-2-methylpropanoate + 2-oxo-n-pentanoate = 2-methyl-3-oxopropanoate + norvaline
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L-tyrosine + 2-oxopentanoate = 3-(4-hydroxyphenyl)-2-oxopropanoate + (2S)-2-aminopentanoate
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L-glutamine + 2-oxovalerate = 2-oxoglutaramate + L-norvaline
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2-oxopentanoic acid = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-hydroxyvalerate + NAD+ = 2-oxovalerate + NADH + H+
show the reaction diagram
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2-hydroxypentanoate + NAD+ = 2-oxopentanoate + NADH + H+
show the reaction diagram
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3-(n-propyl)malate + NAD+ = 2-oxopentanoate + CO2 + NADH
show the reaction diagram
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3-ethylmalate + NAD+ = 3-ethylpyruvate + NADH + CO2
show the reaction diagram
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(S)-2-hydroxyvalerate + ferricytochrome c = 2-oxovalerate + ferrocytochrome c
show the reaction diagram
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D-2-hydroxyvalerate + cytochrome c = 2-oxovalerate + ferrocytochrome c
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2-hydroxypentanoate + O2 = 2-oxopentanoate + H2O2
show the reaction diagram
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2-hydroxy-n-pentanoate + NADH = 2-oxo-n-pentanoate + NADH
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2(R)-hydroxypentanoate + acceptor = 2-oxopentanoate + reduced acceptor
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L-norvaline + H2O + NAD+ = 2-oxopentanoate + NH3 + NADH
show the reaction diagram
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L-norvaline + H2O + NAD+ = 2-oxopentanoate + NH3 + NADH
show the reaction diagram
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L-norvaline + H2O + NAD+ = 2-oxovalerate + NH3 + NADH
show the reaction diagram
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D-norvaline + H2O + O2 = 2-oxopentanoic acid + NH3 + H2O2
show the reaction diagram
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pyruvate + L-norvaline = L-alanine + 2-oxopentanoate
show the reaction diagram
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2-oxosuccinamic acid + L-norvaline = L-asparagine + 2-oxopentanoate
show the reaction diagram
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phenylpyruvate + norvaline = phenylalanine + 2-oxopentanoate
show the reaction diagram
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L-norvaline + 2-oxoglutarate = 2-oxopentanoate + L-glutamate
show the reaction diagram
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norvaline + 2-oxoglutarate = 2-oxovalerate + L-glutamate
show the reaction diagram
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1-palmitoyl-2-oxopentanoyl-sn-glycero-3-phosphocholine + H2O = 1-palmitoyl-sn-glycero-3-phosphocholine + 2-oxopentanoate
show the reaction diagram
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2,3-dihydroxyisovalerate = 2-oxovalerate + H2O
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates through release of branched-chain alpha-keto acid dehydrogenase kinase from the BCKD complex
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Inhibitor in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition
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10 mM, 44.1% inhibition
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non-competitive inhibition at 5 mM
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competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
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competitive
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substrate inhibition
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competitive inhibition
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competitive inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (55 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.64
-
pH 7.5
197
-
pH 7.0, temperature not specified in the publication
0.05
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pH 8.0, 37°C
0.128
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pH 6.7, 30°C
164
-
pH 9.5, 21°C
164
-
-
47.69
-
in 100 mM glycine-KCl-KOH buffer (pH 10), at 25°C
272
-
wild type enzyme, in 50 mM triethanolamine buffer, pH 7.0, at 25°C
6.95
-
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KM Value (86 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.116
-
pH 7.5
0.1
-
pH 7.0, 30°C
3.15
-
pH 8.0, 37°C, wild-type enzyme
0.149
-
pH 6.7, 30°C
49.8
-
wild type enzyme, in 50 mM triethanolamine buffer, pH 7.0, at 25°C
23.8
-
-
94
-
at pH 7.0
25
-
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0.12
-
with L-tryptophan, pH 8.0, 30°C

Ki Value (11 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
9.4
-
-
15
-
above, competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
24.4
-
-
36
-
at pH 7.0
6.7
-
-
20
-
pH 6.0, 30°C, wild-type enzyme and mutant enzyme A460I
3.6
-
pH 8.0, 25°C
1.09
-
pH 8.0, 25°C

References & Links

Links to other databases for 2-Oxopentanoate

ChEBI
PubChem
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PubChem