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MetaCyc Compound: L-arginine

Abbrev Name: arg

Synonyms: 2-amino-5-guanidinovaleric acid, R, arginine, arg, L-arg

Superclasses: an acidall carboxy acidsa carboxylatean amino acida basic amino acid
an acidall carboxy acidsa carboxylatean amino acida polar amino acida positively-charged polar amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida standard alpha amino acid
an acidall carboxy acidsa carboxylatean amino acidan L-amino acid
an amino acid or its derivativean amino acida basic amino acid
an amino acid or its derivativean amino acida polar amino acida positively-charged polar amino acid
an amino acid or its derivativean amino acidan alpha amino acida standard alpha amino acid
an amino acid or its derivativean amino acidan L-amino acid

Chemical Formula: C6H15N4O2

Molecular Weight: 175.21 Daltons

Monoisotopic Molecular Weight: 176.12732577859998 Daltons

L-arginine compound structure

pKa 1: 2.18

SMILES: C(NC(N)=[N+])CCC([N+])C(=O)[O-]

InChI: InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/p+1/t4-/m0/s1

InChIKey: InChIKey=ODKSFYDXXFIFQN-BYPYZUCNSA-O

Unification Links: CAS:74-79-3, ChEBI:32682, ChemSpider:1266045, HMDB:HMDB00517, IAF1260:33707, KEGG:C00062, MetaboLights:MTBLC32682, PubChem:1549073

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 79.88474Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

blasticidin S biosynthesis :
L-arginine → (3S)-β-arginine

clavulanate biosynthesis :
D-glyceraldehyde 3-phosphate + L-arginine → L-N2-(2-carboxyethyl)arginine + phosphate + 2 H+

creatine biosynthesis , guadinomine B biosynthesis :
glycine + L-arginine → guanidinoacetate + L-ornithine

cyanophycin metabolism :
cyanophycin primer-L-aspartate + L-arginine + ATP → cyanophycin + ADP + phosphate
[cyanophycin]-L-aspartate + L-arginine + ATP → cyanophycin + ADP + phosphate

D-cycloserine biosynthesis :
L-arginine + 2-oxoglutarate + oxygen → Nω-hydroxy-L-arginine + succinate + CO2

ethylene biosynthesis II (microbes) :
L-arginine + 2-oxoglutarate + oxygen → (3S)-3-hydroxy-L-arginine + succinate + CO2

ethylene biosynthesis IV :
2-oxoglutarate + L-arginine + oxygen → succinate + CO2 + guanidinium + (S)-1-pyrroline-5-carboxylate + H2O + H+

L-arginine degradation II (AST pathway) :
L-arginine + succinyl-CoA → N2-succinyl-L-arginine + coenzyme A + H+

L-arginine degradation VIII (arginine oxidase pathway) :
L-arginine + oxygen + H2O → ammonium + 5-guanidino-2-oxo-pentanoate + hydrogen peroxide

L-arginine degradation X (arginine monooxygenase pathway) :
L-arginine + oxygen → 4-guanidinobutyramide + CO2 + H2O

L-citrulline-nitric oxide cycle , nitric oxide biosynthesis (plants) :
2 L-arginine + 3 NADPH + H+ + 4 oxygen → 2 L-citrulline + 2 nitric oxide + 3 NADP+ + 4 H2O

peramine biosynthesis :
(S)-1-pyrroline-5-carboxylate + L-arginine + S-adenosyl-L-methionine + 2 ATP → peramine + S-adenosyl-L-homocysteine + 2 AMP + 2 diphosphate + H2O + 2 H+

pyoverdine I biosynthesis :
L-glutamate + L-tyrosine + L-2,4-diaminobutanoate + 2 L-serine + L-arginine + 2 N5-formyl-N5-hydroxy-L-ornithine + L-lysine + 2 L-threonine → ferribactin + 12 H2O + H+

pyruvate fermentation to opines :
D-octopine + NAD+ + H2O ← L-arginine + pyruvate + NADH + H+

rhizocticin A and B biosynthesis :
ATP + 2-amino-4-hydroxy-5-phosphonopentanoate + L-arginine → ADP + L-arginyl-4-hydroxy-5-phosphonopentanoate + phosphate + H+
ATP + L-2-amino-5-phosphono-3-cis-pentenoate + L-arginine → ADP + rhizocticin A + phosphate + H+

streptomycin biosynthesis :
N1-amidinostreptamine 6-phosphate + L-arginine → streptidine 6-phosphate + L-ornithine
L-arginine + 1-amino-1-deoxy-scyllo-inositol 4-phosphate → 1-guanidino-1-deoxy-scyllo-inositol 4-phosphate + L-ornithine

tRNA charging :
a tRNAarg + L-arginine + ATP + H+ → an L-arginyl-[tRNAarg] + AMP + diphosphate

Not in pathways:
D-nopaline + NADP+ + H2O ← L-arginine + 2-oxoglutarate + NADPH + H+
3 2-oxoglutarate + L-arginine + 3 oxygen + 3 H+ → 2 ethylene + 7 CO2 + succinate + guanidinium + (S)-1-pyrroline-5-carboxylate + 3 H2O
2 L-arginine + 3 NAD(P)H + H+ + 4 oxygen → 2 L-citrulline + 2 nitric oxide + 3 NAD(P)+ + 4 H2O
2 L-arginine + 2 NADPH + 2 H+ + 2 oxygen → 2 Nω-hydroxy-L-arginine + 2 NADP+ + 2 H2O
2 L-arginine + 2 NAD(P)H + 2 H+ + 2 oxygen → 2 Nω-hydroxy-L-arginine + 2 NAD(P)+ + 2 H2O

Reactions known to produce the compound:

D-arginine degradation :
5-guanidino-2-oxo-pentanoate + ammonium + NAD(P)H + H+L-arginine + NAD(P)+ + H2O

nopaline degradation :
D-nopaline + an oxidized unknown electron acceptor + H2O → 2-oxoglutarate + L-arginine + an reduced unknown electron acceptor

octopine degradation :
D-octopine + an oxidized unknown electron acceptor + H2O → pyruvate + L-arginine + an reduced unknown electron acceptor

Not in pathways:
Nω-(ADP-D-ribosyl)-L-arginine + H2O → ADP-D-ribose + L-arginine
a [protein] N-terminal L-arginine[periplasm] + H2O[periplasm] → a protein[periplasm] + L-arginine[periplasm] + H+[periplasm]

dimethylsulfoniopropanoate biosynthesis I (Wollastonia) :
S-methyl-L-methionine + a 2-oxo carboxylate + H+ → 3-dimethylsulfoniopropionaldehyde + CO2 + a standard α amino acid

Not in pathways:
amino acids(n) + H2O → a standard α amino acid + amino acids(n-1)
amino acids(n) + H2O → amino acids(n-1) + a standard α amino acid
amino acids(n) + H2O → amino acids(n-1) + a standard α amino acid
a dipetide with L-histidine at the C-terminal + H2O → a standard α amino acid + L-histidine
a peptide with an N-terminal X-L-proline + H2O → a standard α amino acid + a peptide with an N-terminal L-proline + H+
a dipeptide + H2O → 2 amino acids
β-aspartyl dipeptide + H2O → L-aspartate + a standard α amino acid
a protein + H2O → a peptide + a standard α amino acid
a dipeptide + H2O → 2 a standard α amino acid
a peptide + H2O → a standard α amino acid + a peptide
a peptide + H2O → a peptide + a standard α amino acid
a peptide + H2O → a peptide + a standard α amino acid
an oligopeptide + H2O → a peptide + a standard α amino acid
a dipeptide + H2O → a standard α amino acid + a standard α amino acid
a protein + H2O → a peptide + a standard α amino acid
a protein + H2O → a peptide + a standard α amino acid
a protein + H2O → a standard α amino acid + a peptide
a peptide + H2O → a standard α amino acid + a peptide
a protein + H2O → a standard α amino acid + a peptide

Reactions known to both consume and produce the compound:

3-methylarginine biosynthesis , L-arginine degradation XI :
L-arginine + 2-oxoglutarate ↔ L-glutamate + 5-guanidino-2-oxo-pentanoate

arginine dependent acid resistance , L-arginine degradation III (arginine decarboxylase/agmatinase pathway) , L-arginine degradation IV (arginine decarboxylase/agmatine deiminase pathway) , putrescine biosynthesis I , putrescine biosynthesis II , spermidine biosynthesis III :
L-arginine + H+ ↔ CO2 + agmatine

L-arginine biosynthesis I (via L-ornithine) , L-arginine biosynthesis II (acetyl cycle) , L-arginine biosynthesis III (via N-acetyl-L-citrulline) , L-arginine biosynthesis IV (archaebacteria) , L-citrulline-nitric oxide cycle :
L-arginino-succinate ↔ L-arginine + fumarate

L-arginine degradation I (arginase pathway) , L-arginine degradation VI (arginase 2 pathway) , L-arginine degradation VII (arginase 3 pathway) , L-citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis :
L-arginine + H2O ↔ urea + L-ornithine

L-arginine degradation IX (arginine:pyruvate transaminase pathway) :
L-arginine + pyruvate ↔ 5-guanidino-2-oxo-pentanoate + L-alanine

L-arginine degradation V (arginine deiminase pathway) , L-proline biosynthesis II (from arginine) :
L-arginine + H2O ↔ ammonium + L-citrulline

L-arginine degradation XII :
L-arginine + a deaminated amino group donor ↔ 5-guanidino-2-oxo-pentanoate + an aminated amino group donor

putrescine biosynthesis IV :
L-arginine + H2O ↔ urea + L-ornithine
L-arginine + H+ ↔ CO2 + agmatine

urea cycle :
L-arginino-succinate ↔ L-arginine + fumarate
L-arginine + H2O ↔ urea + L-ornithine

Not in pathways:
L-arginine ↔ D-arginine
L-arginine + ATP ↔ Nω-phospho-L-arginine + ADP + H+

dimethylsulfoniopropanoate biosynthesis III (algae) , ethylene biosynthesis III (microbes) :
L-methionine + a 2-oxo carboxylate ↔ 2-oxo-4-methylthiobutanoate + a standard α amino acid

glucosinolate biosynthesis from dihomomethionine :
2-oxo-6-methylthiohexanoate + a standard α amino acid ↔ L-dihomomethionine + a 2-oxo carboxylate

glucosinolate biosynthesis from hexahomomethionine :
2-oxo-10-methylthiodecanoate + a standard α amino acid ↔ hexahomomethionine + a 2-oxo carboxylate

glucosinolate biosynthesis from pentahomomethionine :
2-oxo-9-methylthiononanoate + a standard α amino acid ↔ pentahomomethionine + a 2-oxo carboxylate

glucosinolate biosynthesis from tetrahomomethionine :
2-oxo-8-methylthiooctanoate + a standard α amino acid ↔ tetrahomomethionine + a 2-oxo carboxylate

glucosinolate biosynthesis from trihomomethionine :
2-oxo-7-methylthioheptanoate + a standard α amino acid ↔ trihomomethionine + a 2-oxo carboxylate

L-asparagine degradation II :
a 2-oxo carboxylate + L-asparagine ↔ 2-oxosuccinamate + a standard α amino acid

L-homomethionine biosynthesis :
2-oxo-5-methylthiopentanoate + a standard α amino acid ↔ L-homomethionine + a 2-oxo carboxylate
L-methionine + a 2-oxo carboxylate ↔ 2-oxo-4-methylthiobutanoate + a standard α amino acid

Not in pathways:
L-ornithine + a 2-oxo carboxylate ↔ a standard α amino acid + L-glutamate-5-semialdehyde

Not in pathways:
L-alanine + a 2-oxo carboxylate ↔ pyruvate + an L-amino acid

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ D-erythro-sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
L-arginine + a standard α amino acid + ATP = a dipeptide with N-terminal L-arginine + ADP + phosphate + H+
L-arginine + L-lysine = L-homoarginine + L-ornithine

Not in pathways:
an L-amino acid = a D-amino acid
an L-amino acid + NAD+ + H2O = a 2-oxo carboxylate + ammonium + NADH + H+
an N-carbamoyl-L-amino acid + H2O + 2 H+ = an L-amino acid + ammonium + CO2
S-ureidoglycine + a 2-oxo carboxylate = oxalurate + an L-amino acid

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+

In Transport reactions:
L-glutamine[out] + L-arginine[in] → L-glutamine[in] + L-arginine[out],
L-arginine[out]L-arginine[in],
agmatine[cytosol] + L-arginine[periplasm] → agmatine[periplasm] + L-arginine[cytosol],
ATP + L-arginine[periplasm] + H2O → ADP + L-arginine[cytosol] + phosphate + H+,
a polar amino acid[extracellular space] + ATP + H2O ↔ a polar amino acid[cytosol] + ADP + phosphate

Enzymes activated by L-arginine, sorted by the type of activation, are:

Activator (Allosteric) of: ornithine succinyltransferase [Tricot94] Activator (Mechanism unknown) of: ornithine carbamoyltransferase, catabolic [Ruepp95], glutamate dehydrogenase (NAD-dependent) [Bonete96], ornithine cyclodeaminase [Sans88], arginase

Enzymes inhibited by L-arginine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: agmatinase [Satishchandran86], lysine:cadaverine antiporter [Soksawatmaekhin04] Inhibitor (Mechanism unknown) of: N-acetylglutamate synthase [Marvil77], D-octopine synthase [Schrimsher84], S-methyl-L-methionine decarboxylase [Kocsis00], acetylglutamate kinase, carbamoyl-phosphate synthetase, arginine specific [Paulus79], homocitrate synthase [Wulandari02]

This compound has been characterized as an alternative substrate of the following enzymes: ornithine racemase, L-lysine monooxygenase, guanidinobutyrase, L-lysine α-oxidase, phenylacetyl-coenzyme A:glycine N-acyltransferase, ornaline synthase


References

Bonete96: Bonete MJ, Perez-Pomares F, Ferrer J, Camacho ML (1996). "NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids." Biochim Biophys Acta 1996;1289(1);14-24. PMID: 8605224

Kocsis00: Kocsis MG, Hanson AD (2000). "Biochemical evidence for two novel enzymes in the biosynthesis of 3-dimethylsulfoniopropionate in Spartina alterniflora." Plant Physiol 123(3);1153-61. PMID: 10889264

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Marvil77: Marvil DK, Leisinger T (1977). "N-acetylglutamate synthase of Escherichia coli: purification, characterization, and molecular properties." J Biol Chem 1977;252(10);3295-303. PMID: 16890

Paulus79: Paulus TJ, Switzer RL (1979). "Characterization of pyrimidine-repressible and arginine-repressible carbamyl phosphate synthetases from Bacillus subtilis." J Bacteriol 1979;137(1);82-91. PMID: 216664

Ruepp95: Ruepp A, Muller HN, Lottspeich F, Soppa J (1995). "Catabolic ornithine transcarbamylase of Halobacterium halobium (salinarium): purification, characterization, sequence determination, and evolution." J Bacteriol 1995;177(5);1129-36. PMID: 7868583

Sans88: Sans N, Schindler U, Schroder J (1988). "Ornithine cyclodeaminase from Ti plasmid C58: DNA sequence, enzyme properties and regulation of activity by arginine." Eur J Biochem 173(1);123-30. PMID: 3281832

Satishchandran86: Satishchandran C, Boyle SM (1986). "Purification and properties of agmatine ureohydrolyase, a putrescine biosynthetic enzyme in Escherichia coli." J Bacteriol 1986;165(3);843-8. PMID: 3081491

Schrimsher84: Schrimsher JL, Taylor KB (1984). "Octopine dehydrogenase from Pecten maximus: steady-state mechanism." Biochemistry 23(7);1348-53. PMID: 6722094

Soksawatmaekhin04: Soksawatmaekhin W, Kuraishi A, Sakata K, Kashiwagi K, Igarashi K (2004). "Excretion and uptake of cadaverine by CadB and its physiological functions in Escherichia coli." Mol Microbiol 51(5);1401-12. PMID: 14982633

Tricot94: Tricot C, Vander Wauven C, Wattiez R, Falmagne P, Stalon V (1994). "Purification and properties of a succinyltransferase from Pseudomonas aeruginosa specific for both arginine and ornithine." Eur J Biochem 224(3);853-61. PMID: 7523119

Wulandari02: Wulandari AP, Miyazaki J, Kobashi N, Nishiyama M, Hoshino T, Yamane H (2002). "Characterization of bacterial homocitrate synthase involved in lysine biosynthesis." FEBS Lett 522(1-3);35-40. PMID: 12095615


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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