Ligand L-isoleucine

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Basic Ligand Information

Molecular Structure
Picture of L-isoleucine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H13NO2
L-isoleucine
AGPKZVBTJJNPAG-WHFBIAKZSA-N
Synonyms:
Ile, isoleucine, L-2-amino-3-methyl-pentanoate, L-3-methyl-norvaline, L-Ile, L-threo-isoleucine

Show all pahtways known for Show all pathways known for L-isoleucine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-isoleucine + O2 = ? + H2O2
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L-isoleucine + O2 + NADPH + H+ = (Z)-2-methylbutanal oxime + NADP+ + CO2 + H2O
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L-isoleucine + H2O + NAD+ = 2-oxo-3-methylpentanoate + NH3 + NADH + H+
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ATP + L-isoleucine + tRNAIle = AMP + diphosphate + L-isoleucyl-tRNAIle
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ATP + L-isoleucine + tRNAIle = AMP + diphosphate + L-isoleucyl-tRNAIle
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ATP + L-isoleucine + acetoacetyl-CoA = AMP + diphosphate + tenuazonic acid + CoA
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ATP + (2E)-4-[[(2S)-2-amino-2-carboxyethyl]amino]-4-oxobut-2-enoate + L-isoleucine = ADP + phosphate + N-[(2S)-3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-2-methylpropanoyl]-L-isoleucine
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
Leu-Ile + H2O = Leu + Ile
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jasmonoyl-L-isoleucine + H2O = jasmonic acid + L-isoleucine
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Substrate in Enzyme-catalyzed Reactions (113 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-isoleucine + O2 = ? + H2O2
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L-Ile + O2 = ? + CO2 + H2O
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L-isoleucine + H2O + NAD+ = 2-oxo-3-methylvalerate + NH3 + NADH + H+
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L-isoleucine + H2O + NAD+ = 3-methyl-2-oxopentanoate + NH3 + NADH
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L-isoleucine + H2O + NAD+ = 3-methyl-2-oxopentanoate + NH3 + NADH
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L-isoleucine + H2O + NAD+ = 3-methyl-2-oxopentanoate + NADH + NH3
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L-isoleucine + H2O + 2 cytochrome b = 3-methyl-2-oxo-pentanoate + NH3 + 2 reduced cytochrome b
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L-Ile + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Ile + NAD+
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pyruvate + L-isoleucine = L-alanine + 3-methyl-2-oxopentanoate
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L-isoleucine + glyoxylate = 3-methyl-2-oxopropanoate + glycine
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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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2-oxo-4-methylthiobutanoate + L-isoleucine = L-methionine + 2-oxo-methylvalerate
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L-isoleucine + indole-3-pyruvic acid = 3-methyl-2-oxopentanoate + L-tryptophan
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L-Ile = 2-Methylbutylamine + CO2
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L-Ile = 2-Methylbutylamine + CO2
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L-isoleucine = D-isoleucine
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ATP + L-isoleucine + tRNAIle = AMP + diphosphate + L-isoleucyl-tRNAIle
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ATP + L-isoleucine + tRNAVal = AMP + diphosphate + L-isoleucyl-tRNAVal
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ATP + L-isoleucine + [CmaA-protein-T-domain]-4'-phosphopantetheine = AMP + diphosphate + S-L-isoleucyl-[CmaA-protein-T-domain]-4'-phosphopantetheine
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ATP + L-Glu + L-isoleucine = ADP + phosphate + gamma-L-Glu-L-isoleucine
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L-2-aminoadipate + L-cysteine + L-isoleucine + ATP = L-delta-(aminoadipyl)-L-cysteinyl-D-isoleucine + AMP + diphosphate
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ATP + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine + L-isoleucine = ADP + phosphate + 3-(((2E)-4-amino-4-oxobut-2-enoyl)amino)-L-alanyl-L-isoleucine
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ATP + L-isoleucine + acetoacetyl-CoA = AMP + diphosphate + tenuazonic acid + CoA
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ATP + UDP-N-acetylmuramate + L-Ile = ADP + phosphate + UDP-N-acetylmuramoyl-L-Ile
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ATP + (2E)-4-[[(2S)-2-amino-2-carboxyethyl]amino]-4-oxobut-2-enoate + L-isoleucine = ADP + phosphate + N-[(2S)-3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-2-methylpropanoyl]-L-isoleucine
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[tRNAIle2]-cytidine34 + L-isoleucine + ATP = [tRNAIle2]-2-L-isoleucylcytidine34 + AMP + diphosphate
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Product in Enzyme-catalyzed Reactions (81 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxo-3-methylvalerate + NADPH + NH3 = L-isoleucine + NADP+ + H2O
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2-oxo-4-methylpentanoate + NH3 + NADH = L-Ile + NAD+ + H2O
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3-methyl-2-oxopentanoate + NH3 + NADH + H+ = L-isoleucine + H2O + NAD+
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N-methyl L-isoleucine + 2,6-dichlorophenolindophenol + H2O = L-isoleucine + formaldehyde + reduced 2,6-dichlorophenolindophenol
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beta-alanine + 2-oxoisohexanoate = malonic semialdehyde + L-isoleucine
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L-valine + (S)-3-methyl-2-oxopentanoate = 3-methyl-2-oxobutanoate + L-isoleucine
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L-glutamine + 3-methyl-2-oxo-pentanoate = 2-oxoglutaramate + L-3-methyl-norvaline
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L-kynurenine + 3-methyl-2-oxopentanoate = kynurenic acid + L-isoleucine + H2O
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4-carbamimidamidobenzyl L-isoleucinate + H2O = L-isoleucine + 1-[4-(hydroxymethyl)phenyl]guanidine
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L-isoleucine 2-naphthylamide + H2O = L-isoleucine + 2-naphthylamine
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Ile-2-naphthylamide + H2O = Ile + 2-naphthylamide
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L-Ile-2-naphthylamide + H2O = L-Ile + 2-naphthylamine
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Arg-Ile + H2O = Arg + Ile
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L-Ile-L-Pro-L-Pro + H2O = L-Ile + L-Pro-L-Pro
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L-isoleucyl 4-nitroanilide + H2O = L-isoleucine + 4-nitroaniline
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Met-Ile + H2O = Met + Ile
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Ile-Pro + H2O = Ile + Pro
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Ile-Pro-Ile + H2O = Ile-Pro + Ile
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3-(2-furyl)acryloyl-L-Phe-L-Ile + H2O = 3-(2-furyl)acryloyl-L-Phe + L-Ile
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Ile-Ala + H2O = Ile + Ala
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N-carboxybenzoyl-Ala-Ile + H2O = N-carboxybenzoyl-Ala + L-isoleucine
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2-aminobenzoyl-Phe-Arg-Ile + H2O = 2-aminobenzoyl-Phe-Arg + Ile
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pyroglutamyl-Ile + H2O = pyroglutamate + Ile
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beta-Asp-Ile + H2O = Asp + Ile
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L-isoleucine amide + H2O = L-isoleucine + NH3
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Nalpha-benzyloxycarbonyl-L-Ile + H2O = benzyl alcohol + CO2 + L-Ile
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N-carbamoyl-L-isoleucine + H2O = L-isoleucine + CO2 + NH3
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5-L-glutamyl-L-isoleucine = 5-oxoproline + L-isoleucine
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D-allo-isoleucine = L-isoleucine
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Activator in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.5fold activation at 50 mM
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1% L-isoleucine stimulates activity
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5 mM, 1.72fold activation
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slight activation, kinetics
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13fold activation at 2.5 mM; 3fold activation at 2.5 mM
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inhibitory to enzyme isoform prolidase I, activating isoform prolidase II
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20% activation at 5 mM
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1 mM, relative activity 130%
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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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activation below 0.01 mM, strong inhibition above, 50% inhibition at 0.064 mM
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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, 75% inhibition
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markedly inhibition when arginine but not when ornithine is the acyl acceptor
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weak
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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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20.1% residual activity at 5 mM
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inhibitory to enzyme isoform prolidase I, activating isoform prolidase II
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19% inhibition at 20 mM
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competitive to L-citrulline
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2% cell growth, 1% viability of cells
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Metals and Ions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 450% activity at 1 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (72 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.103
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pH 7.9, 30C
5.8
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pH 10.0, 21C
2.84
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in 100 mM glycine-KCl-KOH buffer (pH 10.4)
5.75
-
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0.012
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pH 7.5, 25C, the assay measures the release of diphosphate by means of a coupled enzyme system in which diphosphate drives the reduction of NAD+ to NADH
5.17
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0.16
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pH 8.0, 22C

KM Value (120 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.3
-
pH 7.9, 30C
250
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6.2
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pyruvate and NADH as cosubstrates
0.47
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with phenylpyruvate, pH 8.0, 30C
2.85
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apparent Km value, at pH 7.4, 37C
153
-
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1.9
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pH 7.5, 37C
0.5
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pH 7.5, 25C, the assay measures the release of diphosphate by means of a coupled enzyme system in which diphosphate drives the reduction of NAD+ to NADH
0.83
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pH 8.0, 22C
0.03
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at pH 8.6 and 25C
40
-
-
0.83
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pH 8.0, 22C

Ki Value (20 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
22
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at pH 7.0
1
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IC50 Value (24 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for L-isoleucine

ChEBI
PubChem
ChEBI
PubChem