Ligand L-valine

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Basic Ligand Information

Molecular Structure
Picture of L-valine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H11NO2
L-valine
KZSNJWFQEVHDMF-BYPYZUCNSA-N
Synonyms:
(2S)-2-amino-3-methylbutanoic acid, L-Val, Val, valine


Show all pahtways known for Show all BRENDA pathways known for L-valine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-valine + O2 = ? + H2O2
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L-valine + O2 + NADPH + H+ = (Z)-2-methylpropanal oxime + NADP+ + CO2 + H2O
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L-valine + NAD(P)+ + H2O = 2-oxoisovalerate + NH3 + NAD(P)H
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ATP + L-valine + tRNAMetG34C36 = AMP + diphosphate + L-valyl-tRNAMetG34C36
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ATP + L-valine + tRNAVal = AMP + diphosphate + L-valyl-tRNAVal
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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-methyl-2-oxobutyrate + L-glutamate = L-valine + 2-oxoglutarate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (153 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-valine + O2 = ? + H2O2
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L-valine + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (E)-2-methylpropanal oxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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L-valine + H2O + NAD+ = 2-oxovalerate + NH3 + NADH + H+
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valine + H2O + NADP+ = 2-oxovalerate + NH3 + NADPH
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L-valine + H2O + NAD+ = 3-methyl-2-oxobutanoate + NH3 + NADH
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L-Val + pyruvate + NADH = ?
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Val + pyruvate + NADH = ?
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L-Val + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Val + NAD+
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L-valine + 2,6-dichlorophenolindophenol + H2O = ? + reduced 2,6-dichlorophenolindophenol
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acetyl-CoA + L-valine = CoA + N-acetyl-L-valine
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pyruvate + L-valine = L-alanine + 3-methyl-2-oxobutanoate
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L-valine + (S)-3-methyl-2-oxopentanoate = 3-methyl-2-oxobutanoate + L-isoleucine
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L-valine + glyoxylate = 3-methyl-2-oxobutanoate + glycine
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valine + pyruvate = 3-methyl-2-oxobutanoate + alanine
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L-valine + alpha-ketomethiobutyrate = 3-methyl-2-oxo-butanoate + L-methionine
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valine + glyoxylate = 3-methyl-2-oxobutanoate + glycine
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2-oxo-4-methylthiobutanoate + L-valine = L-methionine + 2-oxo-isovalerate
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L-valine + indole-3-pyruvic acid = 3-methyl-2-oxobutanoate + L-tryptophan
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L-valine = i-butylamine + CO2
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L-Val = 2-Methylpropylamine + CO2
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L-valine = 2-methylpropanamine + CO2
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L-valine = D-valine
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ATP + L-valine + tRNAMetG34C36 = AMP + diphosphate + L-valyl-tRNAMetG34C36
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ATP + L-valine + tRNAIle = AMP + diphosphate + L-valyl-tRNAIle
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ATP + L-valine + [CmaA-protein-T-domain]-4'-phosphopantetheine = AMP + diphosphate + S-L-valyl-[CmaA-protein-T-domain]-4'-phosphopantetheine
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ATP + L-Glu + L-valine = ADP + phosphate + gamma-L-Glu-L-valine
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ATP + (-)-jasmonate + L-Val = AMP + diphosphate + jasmonoyl-L-Val
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ATP + UDP-N-acetylmuramate + L-Val = ADP + phosphate + UDP-N-acetylmuramoyl-L-Val
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ATP + H2O + L-valine/out = ADP + phosphate + L-valine/in
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Product in Enzyme-catalyzed Reactions (160 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxo-3-methylbutanoate + NH3 + NADH = L-Val + NAD+ + H2O
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2-oxovalerate + NH3 + NADH + H+ = L-valine + H2O + NAD+
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2-oxovalerate + NH3 + NADPH + H+ = L-valine + H2O + NADP+
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N-methyl-L-valine + acceptor + H2O = L-valine + formaldehyde + reduced acceptor
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5-L-glutamyl-L-Val + Gly-Gly = L-Val + 5-L-glutamyl-Gly-Gly
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L-alanine + 2-oxoisopentanoate = pyruvate + L-valine
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beta-alanine + 2-oxoisopentanoate = malonic semialdehyde + L-valine
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histidine + 2-oxoisovalerate = imidazol-5-yl-pyruvate + L-valine
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2-oxoisovalerate + L-glutamate = L-valine + 2-oxoglutarate
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Val-Gly-Gly + H2O = Val + Gly-Gly
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Arg-Val + H2O = Arg + Val
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Val-Trp + H2O = Val + Trp
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Met-Val + H2O = Met + Val
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L-Val-p-nitroanilide + H2O = L-Val + p-nitroaniline
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Val-Leu + H2O = Val + Leu
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Val-4-nitroanilide + H2O = L-valine + p-nitroaniline
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L-Val-7-amido-4-methylcoumarin + H2O = L-Val + 7-amino-4-methylcoumarin
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L-Val-7-amido-4-methylcoumarin + H2O = L-Val + 7-amino-4-methylcoumarin
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Met-Val + H2O = Met + Val
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L-Asp-L-Val + H2O = L-Asp + L-Val
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His-Pro-Val + H2O = His-Pro + Val
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N-benzyloxycarbonyl-Pro-Val + H2O = N-benzyloxycarbonyl-Pro + Val
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Carbobenzoxy-Gly-Val + H2O = Carbobenzoxy-Gly + Val
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2-aminobenzoyl-Phe-Arg-Val + H2O = 2-aminobenzoyl-Phe-Arg + Val
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pyroglutamyl-Val + H2O = pyroglutamate + Val
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beta-Asp-Val + H2O = Asp + Val
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N-Formyl-Met-Val + H2O = N-Formyl-Met + Val
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Benzyloxycarbonyl-Gly-Val + H2O = Benzyloxycarbonyl-Gly + Val
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jasmonoyl-L-valine + H2O = jasmonic acid + L-valine
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L-valineamide + H2O = L-valine + NH3
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L-valinamide + H2O = L-valine + NH3
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N-Benzoyl-Val + H2O = Benzoate + Val
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DL-alpha-aminoisovaleronitrile + H2O = L-valine + NH3
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5-L-glutamyl-L-valine = 5-oxoproline + L-valine
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D-valine = L-Val
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ATP + H2O + L-valine/out = ADP + phosphate + L-valine/in
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Activator in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1% L-valine stimulates activity
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5 mM, 1.47fold activation
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activation
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inhibitory to enzyme isoform prolidase I, activating isoform prolidase II
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1 mM, relative activity 120%
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requirement for branched-chain amino acids, control of the pool of alpha-acetolactate by valine, leucine and isoleucine via allosteric activation, valine is more stimulatory than leucine and isoleucine
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activates
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Inhibitor in Enzyme-catalyzed Reactions (83 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
10 mM, 23% inhibition
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substrate inhibition, noncompetitive
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6% inhibition at 6.67 mM
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5 mM, 23% inhibition
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10 mM, at pH 6.5
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growing this microorganism in the presence of valine diminishes transaminase C activity but does not repress avtA
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competitive inhibitor
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branched chain alpha-amino acids bind at the active site, competitive inhibition mechanism against substrates phosphocreatine and ADP, inhibition kinetics
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23.7% residual activity at 5 mM
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strong inhibition of prolinase activity against Pro-Gly regardless wether MnCl2 is present or not
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inhibitory to enzyme isoform prolidase I, activating isoform prolidase II
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slight inhibition at 20 mM
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weak, liver enzyme
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weak
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less effective inhibitor, Ki-value above 150 mM
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inhibition of biosynthetic and transferase activity
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competitive to L-citrulline
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13% cell growth, 10% viability of cells
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77% residual activity at 5 mM with L-methionine as substrate, 81% residual activity at 50 mM with D-methionine as substrate
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Metals and Ions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 430% activity at 1 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (54 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.91
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25°C, pH 10.4
28.3
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pH 10.0, 21°C
4.95
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in 100 mM glycine-KCl-KOH buffer (pH 10.4)
5.08
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0.214
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pH 7.5, 37°C, recombinant enzyme
0.023
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pH 7.5, 25°C, the assay measures the release of diphosphate by means of a coupled enzyme system in which diphosphate drives the reduction of NAD+ to NADH
21.7
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0.135
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pH 8.0, 22°C

KM Value (116 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2
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25°C, pH 10.4
310
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3
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pyruvate and NADH as cosubstrates
4.5
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with phenylpyruvate, pH 8.0, 30°C
1.77
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apparent Km value, at pH 7.4, 37°C
1100
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5.77
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pH 7.5, 37°C, recombinant enzyme
1.2
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pH 7.5, 25°C, the assay measures the release of diphosphate by means of a coupled enzyme system in which diphosphate drives the reduction of NAD+ to NADH
0.26
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pH 8.0, 22°C
2.49
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at pH 8.6 and 25°C
70
-
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0.26
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pH 8.0, 22°C

Ki Value (27 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
36.8
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140
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at pH 7.0

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
131
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pH 7.0, 30°C

References & Links

Links to other databases for L-valine

ChEBI
PubChem
ChEBI
PubChem