Ligand glyoxylic acid

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Basic Ligand Information

Molecular Structure
Picture of glyoxylic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C2H2O3
glyoxylic acid
HHLFWLYXYJOTON-UHFFFAOYSA-N
Synonyms:
CHO-COOH, glyocylate, glyoxalate, glyoxalic acid, glyoxylate, oxoacetic acid
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for glyoxylic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (47 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glyoxylic acid + O2 + H2O = oxalate + H2O2
show the reaction diagram
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glyoxylate + NH3 + NADH = glycine + H2O + NAD+
show the reaction diagram
-
propanoyl-CoA + glyoxylate = 2-hydroxyglutarate + CoA
show the reaction diagram
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butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA
show the reaction diagram
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glyoxylate + amino acid = ?
show the reaction diagram
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glyoxylate + L-aspartate = glycine + oxaloacetate
show the reaction diagram
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glyoxylate + L-glutamate = glycine + 2-oxoglutarate
show the reaction diagram
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L-serine + glyoxylate = 3-hydroxypyruvate + glycine
show the reaction diagram
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an aromatic amino acid + glyoxylate = an aromatic oxo acid + glycine
show the reaction diagram
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L-kynurenine + glyoxylate = 4-(2-aminophenyl)-2,4-dioxobutanoate + glycine
show the reaction diagram
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4-aminobutanoate + glyoxylate = succinate semialdehyde + glycine
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (51 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
nitrilotriacetate + FMNH2 + H+ + O2 = iminodiacetate + glyoxylate + FMN + H2O
show the reaction diagram
-
-
ethylenediaminetetraacetate + 2 FMNH2 + 2 O2 = ethylenediamine-N,N'-diacetate + 2 glyoxylate + 2 FMN + 2 H2O
show the reaction diagram
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-
glyoxal + H2O + O2 = glyoxylate + H2O2
show the reaction diagram
-
-
glycine + H2O + NAD+ = glyoxylate + NH3 + NADH + H+
show the reaction diagram
-
-
glycine + ferricytochrome c = glyoxylate + ferrocytochrome c + NH3
show the reaction diagram
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Gly + H2O + O2 = glyoxylate + NH3 + H2O2
show the reaction diagram
-
-
allantoate + 3 H2O = glyoxylate + 4 NH3 + 2 CO2
show the reaction diagram
-
-
4-Hydroxy-2-oxoglutarate = Pyruvate + glyoxylate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (347 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glyoxylate + NADPH = glycolate + NADP+
show the reaction diagram
-
glyoxylate + NADPH + H+ = glycolate + NADP+
show the reaction diagram
-
glyoxylate + NADH = glycolate + NAD+
show the reaction diagram
-
glyoxylate + NADH = glycolate + NAD+
show the reaction diagram
-
glyoxylate + NADH + H+ = 2-hydroxypropanoate + NAD+
show the reaction diagram
-
glyoxylic acid + NADPH + H+ = ? + NADP+
show the reaction diagram
-
glyoxylate + NAD(P)H = glycolic acid + NAD(P)+
show the reaction diagram
-
glyoxylate + O2 = oxalate + H2O2
show the reaction diagram
-
glyoxylate + acceptor = oxalate + reduced acceptor
show the reaction diagram
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glyoxylate + NAD+ = ? + NADH
show the reaction diagram
-
glyoxylate + NADH = glyoxal + NAD+
show the reaction diagram
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glyoxylic acid + NAD+ + H2O = 2-phenylbenzoate + NADH + H+
show the reaction diagram
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glyoxylic acid + NAD+ + H2O = oxalic acid + NADH
show the reaction diagram
glyoxylate + O2 = CO2 + CO2
show the reaction diagram
-
glyoxylic acid + H2O + O2 = ?
show the reaction diagram
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glyoxylic acid + O2 + H2O = oxalate + H2O2
show the reaction diagram
-
glyoxylate + CoA + 2 oxidized methyl viologen = ?
show the reaction diagram
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glyoxylate + methyl viologen = ?
show the reaction diagram
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glyoxylate + CoA + 2 oxidized methyl viologen = formyl-CoA + CO2 + 2 reduced methyl viologen + 2 H+
show the reaction diagram
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glyoxylate + CoA + oxidized ferredoxin = formyl-CoA + CO2 + reduced ferredoxin
show the reaction diagram
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glyoxylate + benzyl viologen = oxalic acid + reduced benzyl viologen
show the reaction diagram
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glyoxylate + NH3 + NADH = aminoacetate + NAD+ + H2O
show the reaction diagram
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L-Arg + glyoxylate + NADPH = ?
show the reaction diagram
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L-Ala + glyoxylate + NADH = ?
show the reaction diagram
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Taurine + glyoxylate + NADH = ?
show the reaction diagram
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L-ornithine + glyoxylic acid + NADPH + H+ = ? + NADP+ + H2O
show the reaction diagram
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glyocylate + methylamine + NADPH + H+ = sarcosine + NADP+
show the reaction diagram
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L-Met + glyoxylate + NADH = ?
show the reaction diagram
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(2S)-2-amino-4-[[(1R)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino]butanoate + glyoxylate + NADPH + H+ = ? + NADP+ + H2O
show the reaction diagram
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L-lysine + glyoxylate + NADH = ?
show the reaction diagram
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glyoxylate + 2-oxoglutarate = 5-hydroxy-4-oxopentanoic acid + 2 CO2
show the reaction diagram
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acetyl-CoA + glyoxylate + H2O = ?
show the reaction diagram
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pentanoyl-CoA + glyoxylate + H2O = 3-propylmalate + CoA
show the reaction diagram
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butanoyl-CoA + H2O + glyoxylate = 3-ethylmalate + CoA
show the reaction diagram
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phosphoenolpyruvate + glyoxylate = S-4-hydroxy-2-oxo-1,5-pentanedioate + R-4-hydroxy-2-oxo-1,5-pentanedioate + phosphate
show the reaction diagram
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(S)-ureidoglycine + glyoxylate = N-carbamoyl-2-oxoglycine + glycine
show the reaction diagram
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L-alanine + glyoxylate = pyruvate + glycine
show the reaction diagram
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L-ornithine + glyoxylate = DELTA1-pyrroline-5-carboxylate + glycine
show the reaction diagram
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4-aminobutanoate + glyoxylate = 4-oxobutanoate + glycine
show the reaction diagram
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L-tryptophan + glyoxylate = 3-indole-2-oxopropanoate + glycine
show the reaction diagram
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L-histidine + glyoxylate = imidazol-5-yl-pyruvate + glycine
show the reaction diagram
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(R)-3-amino-2-methylpropanoate + glyoxylate = 2-methyl-3-oxopropanoate + glycine
show the reaction diagram
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L-glutamine + glyoxalate = 2-oxoglutaramate + glycine
show the reaction diagram
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L-phenylalanine + glyoxylate = phenylpyruvate + glycine
show the reaction diagram
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taurine + glyoxylate = 2-sulfoacetaldehyde + glycine
show the reaction diagram
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glyoxylate + L-aspartate = glycine + oxaloacetate
show the reaction diagram
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L-alanine + glyoxylate = pyruvate + glycine
show the reaction diagram
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Pyruvate + glyoxylate = ?
show the reaction diagram
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Pyruvate + glyoxylate = ?
show the reaction diagram
-
Oxaloacetate + glyoxylate = 3-Oxalomalate
show the reaction diagram
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pyruvate + glyoxylate = 4-hydroxy-2-oxoglutarate
show the reaction diagram
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glyoxylate + acetyl-CoA + 5,5'-dithiobis-(2-nitrobenzoic acid) = 5-mercapto-2-nitrobenzoic acid + ?
show the reaction diagram
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ATP + glyoxalate + CoA = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (193 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycolate + ferricytochrome c = glyoxylate + ferrocytochrome c
show the reaction diagram
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-
glycolate + O2 = glyoxylate + H2O2
show the reaction diagram
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-
glycine + O2 = oxoacetic acid + NH3
show the reaction diagram
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-
trichloroethylene + O2 + NADPH = formate + glyoxylate + NADP+
show the reaction diagram
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oxalate + NADH = glyoxylate + NAD+
show the reaction diagram
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glyoxal + NAD+ + H2O = glyoxylate + NADH
show the reaction diagram
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-
glyoxal + NAD+ + H2O = glyoxylate + NADH + H+
show the reaction diagram
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-
glyoxal + H2O + O2 = glyoxylate + H2O2
show the reaction diagram
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-
glyoxal + H2O + O2 = glyoxylate + H2O2
show the reaction diagram
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glyoxal + ferricyanide = oxoacetic acid + ferrocyanide + H+
show the reaction diagram
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-
glycine + ferricytochrome c = glyoxylate + ferrocytochrome c + NH3
show the reaction diagram
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glycine + H2O + O2 = glyoxylate + NH3 + H2O2
show the reaction diagram
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-
2 glyphosate + O2 = 2 aminomethylphosphonate + 2 glyoxylate
show the reaction diagram
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dichloroacetate + glutathione = glyoxylate + HCl + ?
show the reaction diagram
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glycine + 2-oxoglutarate = glyoxylate + L-glutamate
show the reaction diagram
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2-oxoglutaramate + glycine = L-glutamine + glyoxylate
show the reaction diagram
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pyruvate + glycine = L-alanine + glyoxylate
show the reaction diagram
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glycine + 2-oxoglutarate = glyoxylate + glutamate
show the reaction diagram
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dTDP-4-dehydro-6-deoxy-D-glucose + glycine = dTDP-4-amino-4,6-dideoxy-D-galactose + glyoxylate
show the reaction diagram
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glycine + pyruvate = glyoxylate + L-alanine
show the reaction diagram
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glycine + 4,5-dioxopentanoate = 5-aminolevulinate + glyoxylate
show the reaction diagram
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glycine + 2-oxoglutarate = glyoxalate + L-glutamate
show the reaction diagram
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pyruvate + glycine = L-alanine + glyoxylate
show the reaction diagram
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2,3-diketo-1-phosphohexane + H2O = 2-ketopentanoate + formate + glyoxylate + butyrate
show the reaction diagram
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(-)-ureidoglycolate = glyoxylate + urea
show the reaction diagram
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allantoate + 3 H2O = glyoxylate + 4 NH3 + 2 CO2
show the reaction diagram
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chlorofluoroacetic acid + ? = glyoxylate + ?
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50 mM, increasing enzyme activity by 30%
-
activates
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Inhibitor in Enzyme-catalyzed Reactions (116 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
non-competitive inhibition, Ki: 83 mM
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10 mM, 55% inhibition of NADH linked hydroxypyruvate reduction, 15% of NADPH linked reduction, 80% of NAD+ linked glycerate oxidation
strain CETC 978, competitive inhibition
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competitive inhibitor
-
1 mM, 33% inhibition
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2-oxoglutarate dehydrogenase complex
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20 mM, about 40% of the original activity is lost. 2 mM glyoxylate inhibits 6%
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weak
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5 mM, 30% inhibition of reductive amination
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at 20 mM, 30% inhibition
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20 mM, more than 60% inhibition
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inhibitor of octopine formation
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weak
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isozyme AHAS II
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competitive, analysis of pH-dependence of inhibition
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alpha-keto acid acceptor, inhibitor at high concentrations
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at high concentration, transamination between albizziin and glyoxylate
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weak
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at high concentrations
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5 mM, 79% of activity remaining; 5 mM, 83% of activity remaining
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isoenzyme II, french bean
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at concentrations greater than 0.05 mM
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50% activity loss with 0.02 mM glycolate for 10 min at 30°C; strong inhibitor, 50% inhibition at 0.02 mM
-
7.2% residual activity at 8 mM
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12% inhibition at 4 mM
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competitive inhibition
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competitive inhibition
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determmination of an enzyme crystal structure with the inhibitor bound to the active Cys residue of the enzyme as a hemithioacetal, detailed binding structure analysis, overview
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20 mM: 54.1% inhibition, not reversed by 5 mM AMP
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20 mM, 27% inhibition
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-
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32% residual activity at 10 mM
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inhibits the activity in the acetate-forming direction
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3D Structure of Enzyme-Ligand-Complex (PDB) (28 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (82 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
19
-
pH 6.5, 25°C
0.0133
-
pH 6.9, 85°C, under argon
0.074
-
pH 8.0, 22°C
5.29
-
at pH 6.5 and 37°C
48.2
-
pH 7.5, 30°C
113
-
-
3.6
-
pH 7.5, 25°C, recombinant enzyme

KM Value (242 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.38
-
-
18.9
-
pH 6.5, 25°C
25
-
-
46
-
pH 8.0, 70°C
1
-
isoform A
3.7
-
-
8.8
-
L-Met and NADH as cosubstrate
3
-
pH 8.0, 22°C
6.4
-
at pH 7.0
3.6
-
cytosolic isozyme DS-Co, pH 8.6, 37°C
6.7
-
pH 7.1, 37°C
0.077
-
cosubstrate L-asparagine
8
-
pH 8.4, 37ºC
0.43
-
pH 7.1, 25°C, with substrate L-aspartate
7.04
-
pH 7.0, 22°C
0.43
-
-
0.044
-
in 25 mM Bis-Tris-propane/HCl, 100 mM NaCl, pH 8.0 at 75°C
14.3
-
-

Ki Value (29 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
44
-
pH 7.0, 30°C, recombinant enzyme
0.6
-
at pH 7.5 and 33°C
12
-
-
0.01
-
-
1.8
-
-
0.27
-
pH 7.0, 20°C
15
-
in citrate buffer, at pH 4.0 and 22°C
53.1
-
at pH 6.5 and 37°C
0.4
-
pH 7.2
0.5
-
pH 8.0, 37°C
0.4
-
pH 8.1, 30°C
0.4
-
pH 8.0, 25°C
4.3
-
recombinant detagged enzyme, pH 7.0, 37°C
0.21
-
pH 8.0, 25°C
0.14
-
pH and temperature not specified in the publication
0.04
-
-

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.93
-
at pH 6.0 and 37°C

References & Links