Ligand L-aspartate

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Basic Ligand Information

Molecular Structure
Picture of L-aspartate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H7NO4
L-aspartate
CKLJMWTZIZZHCS-REOHCLBHSA-N
Synonyms:
(2S)-2-aminosuccinic acid, (2S)-aspartate, (S)-aspartate, alpha-Asp, alpha-L-Asp, Asp, aspartate, aspartic acid, aspartic acid analogs, L-Asp, L-asparatate, L-aspartate[side 2], L-aspartic acid
Pathway Source
Pathways
MetaCyc
3-dehydroquinate biosynthesis II (archaea), 3-methylarginine biosynthesis, adenosine ribonucleotides de novo biosynthesis, anaerobic energy metabolism (invertebrates, cytosol), beta-alanine biosynthesis III more


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (61 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
L-Asp + H2O + O2 = oxaloacetate + NH3 + H2O2
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show the reaction diagram
glyoxylate + L-aspartate = glycine + oxaloacetate
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L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
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L-aspartate + 3-phenylpyruvate = oxaloacetate + L-phenylalanine
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prephenate + L-aspartate = L-arogenate + oxaloacetate
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show the reaction diagram
L-aspartic acid + NH3 = ?
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L-aspartate = fumarate + NH3
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L-aspartate = D-aspartate
-
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ATP + L-aspartate + NH3 = AMP + diphosphate + L-asparagine
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ATP + L-aspartate + NH3 = ADP + phosphate + L-asparagine
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show the reaction diagram
ATP + dGMP + L-aspartate = ADP + phosphate + 2-amino-2'-deoxy-N6-[(2S)-succino]adenylate
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show the reaction diagram
ATP + H2O + L-Asp/out = ADP + phosphate + L-Asp/in
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In Vivo Product in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
pyridoxamine + oxaloacetate = pyridoxal + L-aspartate
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L-arogenate + oxaloacetate = L-aspartate + prephenate
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Asp-Leu + H2O = Asp + Leu
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L-asparagine + H2O = L-aspartate + NH3
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(indol-3-yl)acetyl-L-aspartate + H2O = (indol-3-yl)acetate + L-aspartate
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L-asparagine + H2O = L-aspartate + NH3
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N-amidino-L-aspartic acid = L-aspartic acid + urea
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3-cyano-L-alanine + H2O = L-aspartate + NH3
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fumarate + NH3 = L-aspartate
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show the reaction diagram
ATP + H2O + L-Asp/out = ADP + phosphate + L-Asp/in
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Substrate in Enzyme-catalyzed Reactions (219 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
L-aspartate + NAD+ = iminopyruvate + CO2 + NADH + H+
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L-Asp + H2O + NAD+ = oxaloacetate + NH3 + NADH
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L-Asp + H2O + O2 = oxaloacetate + NH3 + H2O2
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L-Asp + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-(S)-Asp + NAD+
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L-Asp + dimethylsulfonioacetate = ?
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acetyl-CoA + L-aspartate = CoA + N-acetyl-L-aspartate
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L-arginyl-tRNAArg + L-aspartic acid = tRNAArg + L-Arg-L-Asp
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pyruvate + L-aspartate = L-alanine + oxaloacetate
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2-oxosuccinamic acid + aspartate = L-asparagine + 2-oxo-propane-1,3-dioate
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glyoxylate + L-aspartate = glycine + oxaloacetate
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L-aspartate + 4,5-dioxopentanoate = 5-aminolevulinate + oxaloacetate
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L-aspartate + glyoxylate = 2-oxosuccinate + glycine
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3-(3,4-dihydroxyphenyl)pyruvate + L-aspartate = 3,4-dihydroxy-L-phenylalanine + oxaloacetate
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L-aspartate + pyruvate = oxaloacetate + L-alanine
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L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
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L-aspartic acid + 2-oxoglutarate = oxaloacetate + L-glutamate
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DL-phenylalanine methyl ester + L-aspartic acid = D-phenylalanine methyl ester + L-alpha-aspartame
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L-Asp = ?
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L-Asp = ?
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L-aspartate = 3-aminopropionic acid + CO2
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L-Asp = beta-Ala + CO2
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ATP + aspartate = ADP + alanine + CO2
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L-Asp + H2O = formate + pyruvate + NH3
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L-aspartate = fumarate + NH3
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L-aspartate + pyridoxal 5'-phosphate = 2-oxo-succinate + pyridoxamine 5'-phosphate
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L-aspartate = D-aspartate
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L-aspartate = D-aspartate
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ATP + deamido-NAD+ + Asp = AMP + diphosphate + NAD+ + oxaloacetate
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L-aspartic acid + ATP = poly-L-aspartic acid + ADP + phosphate
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show the reaction diagram
ATP + H2O + aspartate/out = ADP + phosphate + aspartate/in
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Product in Enzyme-catalyzed Reactions (332 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
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show the reaction diagram
oxaloacetate + NH3 + NADH = L-Asp + H2O + NAD+
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methylamine + oxaloacetate + NADPH = aspartic acid + H2O + NADP+
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oxaloacetate + NADPH + NH3 = L-aspartate + NADP+ + H2O
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oxaloacetate + NH3 + NADH + H+ = L-aspartate + H2O + NAD+
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N-methyl L-aspartate + 2,6-dichlorophenolindophenol + H2O = L-aspartate + formaldehyde + reduced 2,6-dichlorophenolindophenol
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L-alanine + oxaloacetate = pyruvate + L-aspartate
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ornithine + oxaloacetate = DELTA1-pyrroline-5-carboxylate + L-aspartate
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L-glutamine + oxaloacetate = 2-oxoglutaramate + L-aspartate
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beta-alanine + oxaloacetic acid = malonic semialdehyde + L-aspartate
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-
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4-hydroxy-L-glutamate + oxaloacetate = 4-hydroxy-2-oxoglutarate + L-aspartate
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3,5-diiodo-L-tyrosine + oxaloacetate = 3,5-diiodo-4-hydroxyphenylpyruvate + L-aspartate
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pyridoxamine + oxaloacetate = pyridoxal + L-aspartate
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L-lysine + oxaloacetate = 2-aminoadipate 6-semialdehyde + L-aspartate
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(R)-3-amino-2-methylpropanoate + oxaloacetate = 2-methyl-3-oxopropanoate + L-aspartate
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D-methionine + oxaloacetate = 4-methylthio-2-oxobutanoate + L-aspartate
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3-(3,4-dihydroxyphenyl)-L-alanine + oxaloacetic acid = 3-(3,4-dihydroxyphenyl)pyruvate + L-aspartate
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L-glutamine + oxaloacetate = 2-oxoglutaramate + L-aspartate
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L-serine + oxaloacetate = 3-hydroxypyruvate + L-aspartate
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L-leucine + oxaloacetate = 4-methyl-2-oxopentanoate + L-aspartate
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L-glutamine + oxaloacetate = 2-oxoglutaramate + L-aspartate
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L-methionine + oxaloacetate = 4-methylsulfanyl-2-oxobutanoate + L-aspartate
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alpha-ketobutyric acid + putrescine = L-aspartate + 4-aminobutanal
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chorismate + L-asparagine = 4-amino-4-deoxychorismate + L-aspartate
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L-histidinol phosphate + oxaloacetate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-aspartate
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(S)-1-phenylethylamine + oxaloacetate = acetophenone + L-aspartate
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(2S,3S,5R,10S,12R,14R,15S,16S)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol + oxaloacetate = (3S,5R,10S,12R,14R,15S,16S)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-one + L-aspartate
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L-aspartate dimethyl ester + H2O = L-aspartate + methanol
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Ala-Asp + H2O = Ala + Asp
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Asn + H2O = Asp + NH3
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cholecystokinin octapeptide + H2O = tyrosine sulfate + Asp + Met + Gly + Trp + Met-Asp-Phe-NH2
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L-Asp-7-amido-4-methylcoumarin + H2O = 7-amino-4-methylcoumarin + L-Asp
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Pro-Asp + H2O = Pro + Asp
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L-Asp-Pro-7-amido-4-carbamoylmethylcoumarin + H2O = L-Asp + Pro-7-amido-4-carbamoylmethylcoumarin
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L-Asp-7-amido-4-methylcoumarin + H2O = L-Asp + 7-amino-4-methylcoumarin
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Asp-Ala + H2O = Asp + Ala
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Pro-Asp + H2O = Pro + Asp
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N-acetyl-L-aspartate = acetate + L-aspartate
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L-Asp-L-Glu + H2O = L-Asp + L-Glu
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[stathmin]-KNKESKDPADETEAD + H2O = [stathmin]-KNKESKDPADETEA + Asp
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benzyloxycarbonyl-Asp + H2O = L-aspartate + benzyloxycarbonate
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2-aminobenzoyl-Phe-Arg-Asp + H2O = 2-aminobenzoyl-Phe-Arg + Asp
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N-acetyl-Ala-Asp + H2O = N-acetyl-Ala + Asp
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N2-L-Asp-ubiquitin + H2O = ubiquitin + L-Asp
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pyroglutamyl-Asp + H2O = pyroglutamate + Asp
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GLLVDLGL + H2O = GLLV + Asp + LGL
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NQDVDAAVRGIK + H2O = NQDV + L-Asp + AAVRGIK
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LTEKRDSIS + H2O = LTEKR + L-Asp + Ser-Ile-Ser
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N-phenylacetyl-Asp + H2O = phenylacetic acid + Asp
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biotinyl-L-aspartate + H2O = biotin + L-aspartate
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L-asparagine + H2O = L-aspartate + NH3
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show the reaction diagram
N-lauroyl-L-aspartate + H2O = lauroate + L-aspartate
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L-asparagine + H2O = L-aspartate + NH3
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N-acetyl-L-aspartate + H2O = acetate + L-aspartate
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L-ureidosuccinic acid + H2O = L-aspartic acid + CO2 + NH3
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Gly-D-Asp + H2O = Glycine + Asp
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DGDPP + H2O = L-Asp + GDPP
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beta-cyano-L-alanine + H2O = asparagine + aspartic acid
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beta-aspartyl phosphate + H2O = aspartate + phosphate
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show the reaction diagram
5-L-glutamyl-L-aspartate = 5-oxoproline + L-aspartate
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D-aspartate = L-aspartate
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AMP-Asp + diphosphate = ATP + L-Asp
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ATP + [L-Asp(4-L-Arg)]3-L-Asp + L-Arg = ADP + phosphate + [L-Asp(4-L-Arg)]4 + L-Asp
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ATP + ribose 5-phosphate + Asn = ADP + phosphate + 5-phosphoribosylamine + Asp
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ATP + deamido-NAD+ + Asn = AMP + diphosphate + NAD+ + Asp
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ATP + Glu-tRNAGln + Asn = ADP + phosphate + Gln-tRNAGln + Asp
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ATP + H2O + aspartate/out = ADP + phosphate + aspartate/in
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Activator in Enzyme-catalyzed Reactions (40 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (138 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
slightly competitive to malate, only slight inhibition below pH 6.0
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competitive, 94% inhibition at 10 mM
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25% inhibition at 16 mM
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92% inhibition at 30 mM
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aspartic acid decreases enzyme activity to 50% at a concentration of 1.5 mM. Replacing the sulfydryl by the uncharged hydroxyl group of serine does not affect enzyme activity.
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67% inhibition at 10 mM aspartic acid in the growth medium
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competitive inhibitor with respect to alpha-aminoadipate
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no inhibition
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neonatal pretreatment, which reduces circulating growth hormone levels, decreases male aldehyde oxidase activity to female levels; neonatal pretreatment, which reduces circulating growth hormone levels, decreases male aldehyde oxidase activity to female levels; neonatal pretreatment, which reduces circulating growth hormone levels, decreases male aldehyde oxidase activity to female levels; neonatal pretreatment, which reduces circulating growth hormone levels, decreases male aldehyde oxidase activity to female levels; neonatal pretreatment, which reduces circulating growth hormone levels, decreases male aldehyde oxidase activity to female levels
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50% inhibition at concentrations below 7 mM
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10 mM, 60% inhibition
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weak inhibition, competitive with 2-oxoglutarate
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weak
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inhibition of NADPH linked reaction, activation of NAD(H) linked reaction
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substrate inactivation
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slight inhibition at 100 mM
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competitive inhibition
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slight
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10 mM Asp inhibits BHMT
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0.015 mM, 26% inhibition
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at high concentrations
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20 mM, 30% inhibition
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1 mM, 23% inhibition
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1 mM, 37% inhibition
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IC50: 0.3 mM
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inhibits tyrosine transamination
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weak, competitive against 2-oxoglutarate
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weak, asparagine/pyruvate reaction
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no inhibition by D-aspartate
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with L-tyrosine and 2-oxoglutarate or oxaloacetate as substrates
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0.72 mM, 50% inhibition of brain KAT I, 0.073 mM, 50% inhibition of brain KAT II
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specific inhibitor of KAT IV
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competitive, 1 mM
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slight
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31% inhibition at 0.2 mM, cPK1; 6% inhibition at 0.2 mM, cPK3
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only isozyme PKp, not PKc
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0.02-0.15 mM, causes inactivation and unfolding of arginine kinase
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5fold higher concentration than L-Arg, 25% inhibition
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inhibitory above 2.8 mM
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10 mM, 60% inhibition
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competitive
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21.8% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Asp-4-nitroanilide, and 24.0% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Glu-4-nitroanilide
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39.5% inhibition at 10 mM, no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Asp-4-nitroanilide, and 33.8% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Glu-4-nitroanilide
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21.8% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Asp-4-nitroanilide, and 24.0% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Glu-4-nitroanilide
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39.5% inhibition at 10 mM, no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Asp-4-nitroanilide, and 33.8% inhibition at 10 mM and no inhibition at 0.1-1.0 mM, product inhibition versus substrate L-Glu-4-nitroanilide
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weak inhibition of hydrolysis of 4-amino-N10-methylpteroylglutamic acid
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0.1 mM, 42% inhibition
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competitive
product inhibition at pH 8.5
0.002 M, 20-25% inhibition
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40% inhibition at 1 mM
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competitive inhibitor
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competitive inhibition, Ki: glutaminase activity 0.16 mM, asparaginase activity 0.53 mM
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strong inhibition, 8 mM: 53% of activity compared to H2O
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competitive inhibition
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29% inhibition at 10 mM
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inhibition via chelating Mn2+, allantoate protects and reverses
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competitive inhibition, 10 mM
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substrate inhibition
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D-Asp, weak
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inhibits 20% at 1 mM
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1 mM, 85% residual activity for wild-type, 60% for mutant K954E, respectively
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10 mM, 41% inhibition in presence of 5 mM Mg2+ or 15 mM Mg2+
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2 mM, 95% decreases of activity of PEPC1 at pH 7.3, 49% decrease in activity of PEPC2 at pH 8
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4 mM, complete inhibition
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98% residual activity at 2 mM
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allosteric inhibitor
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at pH 7.2, weak competitive inhibition for enzyme form PEPC I, strong competitive inhibition for enzyme form PEPC II and enzyme form PEPC III
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IC50 of phospho-PEPC1: 0.35 mM, IC50 of dephospho-PEPC1: 0.32 mM; IC50 of phospho-PEPC2: 2.6 mM, IC50 of dephospho-PEPC2: 4.5 mM, enzyme form PEPC2
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isoenzyme PEPC1 is more sensitive to inhibition than isoenzyme PEPC2
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L-Asp competitively inhibits the enzyme with respect to the substrate, Mg2+-phosphoenolpyruvate
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L-Asp, competitive
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more sensitive to inhibition by Asp at pH 9.0 than at pH 7.0
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potent inhibitor at pH 7 in absence of glycerol, but its effectiveness is decreased by raising the pH to 8 and/or by adding glycerol
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the enzyme loses about 95% activity when the aspartate concentration is more than 2 mM
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very low sensitivities to allosteric inhibitors aspartate and glutamate; very low sensitivities to allosteric inhibitors aspartate and glutamate
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40 mM, 20% inhibition
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competitive inhibition, L-aspartate 4-semialdehyde as varied substrate
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2 mM, 53% residual activity
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competitive
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inhibition of biosynthetic and transferase activity
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more inhibitory for enzyme from strain SA0 than for enzyme from SA1
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with NH4+ is nitrogen donor
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24% inhibition at 1 mM
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uncompetitive
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47% inhibition at 10 mM
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6.4% inhibition at 10 mM
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activity decreases sharply as the aspartate concentration increases up to 20 mM, beyond that point the activity decreases with a slower effect, 20% remaining activity at 20 mM
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allosteric inhibitor
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antagonizes activation by acetyl-CoA
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competitive with respect to HCO3-, non-competitive with respect to pyruvate and MgATP2-
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enhances the rate of inactivation observed on incubation at 4 C in the presence of 0.5 M KCl. At low concentrations it enhances the effectiveness of inhibition by 2-oxoglutarate
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L-Aspartate competitively inhibits hydrogencarbonate-dependent MgATP cleavage with respect to MgATP and also probably inhibits carboxybiotin formation and/or translocation of the carboxybiotin to the site of pyruvate carboxylation. Unlike acetyl-CoA, L-aspartate has no effect on the coupling between MgATP cleavage and oxaloacetate formation
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no inhibition
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slight inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (847 results)

EC NUMBER
ENZYME 3D STRUCTURE