Ligand L-arginine

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Basic Ligand Information

Molecular Structure
Picture of L-arginine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H14N4O2
L-arginine
ODKSFYDXXFIFQN-BYPYZUCNSA-N
Synonyms:
Arg, arginine, arginine derivatives, L-2-amino-5-guanidinopentanoate, L-Arg, Nalpha-L-arginine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (41 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-arginine + O2 = ?
show the reaction diagram
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3 2-oxoglutarate + L-arginine + 3 O2 = 2 C2H4 + succinate + 7 CO2 + 3 H2O + guanidine + L-DELTA1-pyrroline-5-carboxylate
show the reaction diagram
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L-arginine + O2 + H2O = 5-carbamidamido-2-oxopentanoate + NH3 + H2O2
show the reaction diagram
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L-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2
show the reaction diagram
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L-arginine + pyruvate + NADH + H+ = N2-(D-1-carboxyethyl)-L-arginine + NAD+ + H2O
show the reaction diagram
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L-arginine + 1-amino-1-deoxy-scyllo-inositol 4-phosphate = L-ornithine + 1-guanidino-1-deoxy-scyllo-inositol 4-phosphate
show the reaction diagram
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succinyl-CoA + L-arginine = CoA + N2-succinyl-L-arginine
show the reaction diagram
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D-glyceraldehyde 3-phosphate + L-arginine = N2-(2-carboxyethyl)-L-arginine + phosphate
show the reaction diagram
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L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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fumarate + L-arginine = 2-(Nomega-L-arginino)succinate
show the reaction diagram
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L-arginine = D-arginine
show the reaction diagram
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ATP + L-tyrosine + L-arginine = L-tyrosyl-L-arginine + AMP + diphosphate
show the reaction diagram
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ATP + [L-Asp(4-L-Arg)]n-L-Asp + L-Arg = ADP + phosphate + [L-Asp(4-L-Arg)]n+1
show the reaction diagram
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ATP + L-arginine + an L-amino acid = ADP + phosphate + an L-arginyl-L-amino acid
show the reaction diagram
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ATP + H2O + L-Arg/out = ADP + phosphate + L-Arg/in
show the reaction diagram
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ATP + H2O + arginine/out = ADP + phosphate + arginine/in
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-ornithine + guanidinoacetate = L-arginine + glycine
show the reaction diagram
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-
ADP + Nomega-phospho-L-Arg = ATP + L-arginine
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-
angiotensin III + H2O = angiotensin IV + Arg
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angiotensin III + H2O = angiotensin IV + Arg
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bradykinin + H2O = Arg + des-Arg-bradykinin
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His-Lys-Asp-Met-Gln-Leu-Gly-Arg + H2O = His-Lys-Asp-Met-Gln-Leu-Gly + Arg
show the reaction diagram
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D-arginine = L-arginine
show the reaction diagram
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ATP + H2O + L-Arg/out = ADP + phosphate + L-Arg/in
show the reaction diagram
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ATP + H2O + arginine/out = ADP + phosphate + arginine/in
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (207 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3 2-oxoglutarate + L-arginine + 3 O2 = 2 C2H4 + succinate + 7 CO2 + 3 H2O + guanidine + L-DELTA1-pyrroline-5-carboxylate
show the reaction diagram
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L-arginine + 2-oxoglutarate + O2 = (3S)-3-hydroxy-L-arginine + succinate + CO2
show the reaction diagram
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L-arginine + H2O + NAD(P)+ = 5-guanidino-2-oxopentanoate + NH3 + NAD(P)H + H+
show the reaction diagram
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L-arginine + H2O + NAD+ = ? + NH3 + NADH
show the reaction diagram
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L-arginine + H2O + O2 = 5-guanidino-2-oxopentanoate + NH3 + H2O2
show the reaction diagram
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L-arginine + H2O + 2 cytochrome b = 2-oxo-5-guanidinopentanoic acid + NH3 + 2 reduced cytochrome b
show the reaction diagram
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L-arginine + 2,6-dichlorophenolindophenol + H2O = ? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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succinyl-CoA + L-arginine = CoA + N2-succinyl-L-arginine
show the reaction diagram
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benzoyl-CoA + arginine = CoA + ornithuric acid
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phenylacetyl-CoA + L-arginine = ? + CoA
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acetyl-CoA + L-arginine = CoA + ?
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arginine + NAD+ = nicotinamide + ADP-ribose-L-arginine
show the reaction diagram
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D-glyceraldehyde 3-phosphate + L-arginine = N2-(2-carboxyethyl)-L-arginine + phosphate
show the reaction diagram
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arginine + pyruvate = 2-oxo-5-guanidinovaleric acid + L-alanine
show the reaction diagram
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L-arginine + 2-oxoglutarate = 2-oxo-5-guanidinopentanoate + L-glutamate
show the reaction diagram
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L-arginine + 4,5-dioxopentanoate = 5-aminolevulinate + 5-guanidino-2-oxopentanoate
show the reaction diagram
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L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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arginine + alpha-ketomethiobutyrate = ? + methionine
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L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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L-arginine + pyruvate = 5-guanidino-2-oxopentanoate + L-alanine
show the reaction diagram
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3-(imidazol-4-yl)-2-oxopropyl phosphate + L-arginine = L-histidinol phosphate + 2-oxo-5-guanidinopentanoate
show the reaction diagram
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ATP + L-Arg = ADP + N5-phosphoarginine
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ATP + arginine = ADP + ?
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ATP + arginine = ADP + phosphoarginine
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Leu + Arg = Tyr + Gly
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L-arginine + H2O = ?
show the reaction diagram
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benzyloxycarbonyl-Ala methyl ester + L-Arg = benzyloxycarbonyl-Ala-Arg-OH
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L-arginine + H2O = L-ornithine + urea
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L-arginine + H2O = ? + NH3
show the reaction diagram
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L-arginine + H2O = ?
show the reaction diagram
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Arg = 1-Amino-4-guanidinobutane
show the reaction diagram
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L-arginine = ?
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L-arginine = agmatine + CO2
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L-arginine + pyridoxal 5'-phosphate = 2-oxo-5-guanidinopentanoate + pyridoxamine 5'-phosphate
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L-arginine = D-arginine
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L-arginine = D-arginine
show the reaction diagram
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L-arginine = D-arginine
show the reaction diagram
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L-arginine = D-arginine
show the reaction diagram
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ATP + L-arginine + tRNALys = AMP + L-arginyl-tRNALys + diphosphate
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ATP + Arg + beta-Ala = AMP + phosphate + beta-Ala-Arg
show the reaction diagram
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ATP + H2O + arginine/out = ADP + phosphate + arginine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (356 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-guanidino-2-oxopentanoate + NH3 + NAD(P)H + H+ = L-arginine + H2O + NAD(P)+
show the reaction diagram
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L-canavanine + L-ornithine = L-canaline + L-arginine
show the reaction diagram
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L-glutamine + alpha-keto-delta-carbamidovalerate = 2-oxoglutaramate + L-arginine
show the reaction diagram
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L-histidinol phosphate + 2-oxo-5-guanidinopentanoate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-arginine
show the reaction diagram
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L-arginine methyl ester + H2O = L-arginine + methanol
show the reaction diagram
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arginine phosphate + H2O = Arg + phosphate
show the reaction diagram
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Arg-Trp + H2O = Arg + Trp
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Arg 2-naphthylamide + H2O = Arg + 2-naphthylamine
show the reaction diagram
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L-arginyl-2-naphthylamide + H2O = L-arginine + 2-naphthylamine
show the reaction diagram
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L-arginyl 4-nitroanilide + H2O = L-arginine + 4-nitroaniline
show the reaction diagram
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L-Arg-7-amido-4-methylcoumarin + H2O = L-Arg + 7-amino-4-methylcoumarin
show the reaction diagram
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L-arginyl 4-nitroanilide + H2O = L-arginine + 4-nitroaniline
show the reaction diagram
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Leu-Arg + H2O = Leu + Arg
show the reaction diagram
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L-Arg-4-nitroanilide + H2O = L-Arg + 4-nitroaniline
show the reaction diagram
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L-Ala-L-Pro-L-Arg + H2O = L-Ala-L-Pro + L-Arg
show the reaction diagram
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Hippuryl-L-Arg + H2O = Hippuric acid + L-Arg
show the reaction diagram
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N-benzyloxycarbonyl-Ala-Arg + H2O = N-benzyloxycarbonyl-Ala + L-arginine
show the reaction diagram
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N-carboxybenzoyl-Ala-Arg + H2O = N-carboxybenzoyl-Ala + L-arginine
show the reaction diagram
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pyroglutamyl-Arg + H2O = pyroglutamate + Arg
show the reaction diagram
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Arg-4-nitroanilide + H2O = Arg + 4-nitroaniline
show the reaction diagram
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Nalpha-benzoyl-L-Arg + H2O = benzoic acid + L-Arg
show the reaction diagram
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alpha-N-acetyl-Leu-Lys-Arg-4-nitroanilide + H2O = alpha-N-acetyl-Leu-Lys + Arg + 4-nitroaniline
show the reaction diagram
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Arg-4-methyl-coumaryl-7-amide + H2O = Arg + 7-amino-4-methylcoumarin
show the reaction diagram
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Arg-4-methylcoumarin 7-amide + H2O = Arg + 7-amino-4-methylcoumarin
show the reaction diagram
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L-Arg-7-amido-4-methylcoumarin + H2O = L-Arg + 7-amino-4-methylcoumarin
show the reaction diagram
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Arg-7-amido-4-methylcoumarin + H2O = Arg + 7-amino-4-methylcoumarin
show the reaction diagram
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Nalpha-DL-arginine 4-nitroanilide + H2O = Nalpha-L-arginine + 4-nitroaniline
show the reaction diagram
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L-Arg methyl ester + H2O = L-Arg + methanol
show the reaction diagram
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ELSKRSSPS + H2O = ELSK + L-Arg + SSPS
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L-Arg beta-naphthylamide + H2O = Arg + beta-naphthylamine
show the reaction diagram
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N-acetylarginine + H2O = acetate + arginine
show the reaction diagram
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phospho-L-arginine + H2O = L-arginine + phosphate
show the reaction diagram
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(Nomega-L-arginino)succinate = fumarate + L-arginine
show the reaction diagram
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D-arginine = L-arginine
show the reaction diagram
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ATP + H2O + arginine/out = ADP + phosphate + arginine/in
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
L-Arg has major positive influence on refolding. L-Arg is the key player in the refolding of human G6PD, preventing the aggregation of folding intermediate
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highly specific for cofactor L-arginine, KM value 0.018 mM
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enhances the rate of O2 activation, allosteric regulator
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L-arginine strongly stimulates oxygen consumption of eNOS and inhibits that of nNOS, nonhydrolyzable L-arginine analogues are not stimulatory
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highly specific for cofactor L-arginine, KM value 0.018 mM
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activation
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50 mM, 2fold activatin
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allosteric activator of the ornithine succinyltransferase activity
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stimulates the activity via conformational changes that occur upon binding to the amino acid-binding-domain
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induces the L-ATase activity at least 76fold in an aruF mutant strain, but not in the wild-type strain PAO1
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slight activation is observed at 1 mM L-arginine
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8% activation at 10 mM
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strong substrate activation of the kidney enzyme at concentrations above 4 mM
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but it inhibits at concentrations about 14 mM agmatine
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can partially substitute for phenylhydrazine, 19% of the activity with phenylhydrazine
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stimulates
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up to 1.2fold activation
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Inhibitor in Enzyme-catalyzed Reactions (123 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
uncompetitive
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1% L-arginine represses transcription
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less than 45% inhibition
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20 mM, complete inhibition
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; pH 7.6, 30°C
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substrate inhibition
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weak
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inhibition of alpha-S1-casein-dependent reaction
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98% inhibition at 0.01 mM, 95% inhibition at 0.1 mM and 84% inhibition at 1 mM
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fully reversed by addition of pyridoxal phosphate, 28% inhibition at 10 mM after 20 min
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10 mM, 13% inhibition
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slight inhibition
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slight
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treatment with single injection or for one week with daily injection of saline or L-Arg plus Nomega-nitro-L-arginine methyl ester or alpha-tocopherol plus ascorbic acid. Total and cytosolic creatine kinase activities are significantly inhibitied by L-arginine adminstration, mitochondrial enzyme activity is not affected. simultaneous injection of Nomega-nitro-L-arginine methyl ester and alpha-tocopherol plus ascorbic acid prevent inhibition
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0.01 M, 47% inhibition
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21% inhibition at 0.1 mM
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19.3% residual activity at 5 mM
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esterolytic activity
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complete inhibition of coaggregation of Porphyromonas gingivalis with other oral bacteria by L- and D-arginine
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inhibition of the recombinant enzyme at high concentrations
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competitive inhibition, 10 mM
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weak
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strong inhibition
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noncompetitive versus argininosuccinate
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8% cell growth, 25% viability of cells
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (266 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
43.5
-
pH 8.0, 30°C
1.08
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875
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per active site, pH 8.5, 30°C
0.12
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pH 8.0, 25°C
38.6
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calculated, pH 9.0, 37°C, coupled reaction with NAD+ and L-alanine dehydrogenase; pH 9.0, 37°C
0.0859
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pH 7.5, 37°C, recombinant enzyme
0.0012
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transamination

KM Value (517 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.3
-
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3.4
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pH 8.0, 30°C
0.0082
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pH 7.5, 25°C
3.2
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pH 8.5
8
-
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0.74
-
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210
-
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130
-
pH 8.0, 25°C