Record Information
Version2.0
Creation Date2012-05-31 10:27:12 -0600
Update Date2015-09-13 12:56:08 -0600
Secondary Accession Numbers
  • ECMDB00517
Identification
Name:L-Arginine
Description:Arginine is an amino acid that is physiologically active in the L-form. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing and hydrophobic, whereas the end of the side chain is a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. The main catabolic arginine pathway of Escherichia coli K-12 is the succinyltransferase pathway. (PMID: 9696779)
Structure
Thumb
Synonyms:
  • (S)-2-amino-5-[(aminoiminomethyl)amino]-Pentanoate
  • (S)-2-amino-5-[(aminoiminomethyl)amino]-Pentanoic acid
  • (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate
  • (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid
  • 2-Amino-5-guanidinovalerate
  • 2-Amino-5-guanidinovaleric acid
  • 5-[(Aminoiminomethyl)amino]-L-Norvaline
  • Arg
  • Arginine
  • L-(+)-Arginine
  • L-a-Amino-D-guanidinovalerate
  • L-a-Amino-D-guanidinovaleric acid
  • L-a-Amino-delta-guanidinovalerate
  • L-a-Amino-delta-guanidinovaleric acid
  • L-a-amino-δ-Guanidinovalerate
  • L-a-amino-δ-Guanidinovaleric acid
  • L-alpha-Amino-delta-guanidinovalerate
  • L-alpha-Amino-delta-guanidinovaleric acid
  • L-α-amino-δ-Guanidinovalerate
  • L-α-amino-δ-Guanidinovaleric acid
  • N5-(aminoiminomethyl)-L-Ornithine
  • R
Chemical Formula:C6H14N4O2
Weight:Average: 174.201
Monoisotopic: 174.111675712
InChI Key:ODKSFYDXXFIFQN-BYPYZUCNSA-N
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)/t4-/m0/s1
CAS number:74-79-3
IUPAC Name:(2S)-2-amino-5-carbamimidamidopentanoic acid
Traditional IUPAC Name:L-arginine
SMILES:N[C@@H](CCCNC(N)=N)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:1
Melting point:222 °C
Experimental Properties:
PropertyValueSource
Water Solubility:182 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 182.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-4.20 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.28 mg/mLALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m3·mol-1ChemAxon
Polarizability17.8 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + L-Arginine > ADP + L-Arginine + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Arginine > ADP + L-Arginine + Hydrogen ion + Phosphate
L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine
L-Arginine + Adenosine triphosphate + tRNA(Arg) + tRNA(Arg) <> Adenosine monophosphate + L-Arginyl-tRNA(Arg) + Pyrophosphate + L-Arginyl-tRNA(Arg)
L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide
Argininosuccinic acid <> L-Arginine + Fumaric acid
L-Arginine + Hydrogen ion > Agmatine + Carbon dioxide
L-Arginine <> Agmatine + Carbon dioxide
Succinyl-CoA + L-Arginine <> Coenzyme A + N2-Succinyl-L-arginine
Argininosuccinic acid <> Fumaric acid + L-Arginine
Adenosine triphosphate + L-Arginine + tRNA(Arg) <> Adenosine monophosphate + Pyrophosphate + L-Arginyl-tRNA(Arg)
Adenosine triphosphate + L-Arginine + Water > ADP + Phosphate + L-Arginine + Hydrogen ion
Adenosine triphosphate + L-Arginine + Water > ADP + Phosphate + L-Arginine + Hydrogen ion
Hydrogen ion + L-Arginine > Carbon dioxide + Agmatine
L-Arginine + Succinyl-CoA > Hydrogen ion + N2-Succinyl-L-arginine + Coenzyme A
L-arginino-succinate <> L-Arginine + Fumaric acid
General-Protein-Substrates L-Arginine + Peptides
L-Arginine > Agmatine + Carbon dioxide
2-(N(omega)-L-arginino)succinate > Fumaric acid + L-Arginine
Succinyl-CoA + L-Arginine > CoA + N2-Succinyl-L-arginine
L-Arginine > Agmatine + Carbon dioxide
Adenosine triphosphate + L-Arginine + tRNA(Arg) > Adenosine monophosphate + Pyrophosphate + L-arginyl-tRNA(Arg)
Argininosuccinic acid > Fumaric acid + L-Arginine
L-Arginine + Succinyl-CoA + Succinyl-CoA > Coenzyme A + Hydrogen ion + N2-succinyl-L-arginine + N2-succinyl-L-arginine
L-Arginine + Hydrogen ion + Carbon dioxide > Agmatine

SMPDB Pathways:
Aspartate metabolismPW000787 Pw000787Pw000787 greyscalePw000787 simple
arginine metabolismPW000790 Pw000790Pw000790 greyscalePw000790 simple
tRNA Charging 2PW000803 Pw000803Pw000803 greyscalePw000803 simple
tRNA chargingPW000799 Pw000799Pw000799 greyscalePw000799 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
569± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
58± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
390± 24 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0a4i-1910000000-0191c1a63652c493660bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9810000000-eb6eb73302b678cf0a24View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-9700000000-e47b41cff0e873f53932View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1920000000-8ae5af11398835d26bedView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00dl-9100000000-60db59de76b9a9b5bfc8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0a4i-1910000000-0191c1a63652c493660bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9810000000-eb6eb73302b678cf0a24View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-9700000000-e47b41cff0e873f53932View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0a4i-1920000000-8ae5af11398835d26bedView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0900000000-afc3ca93f8fbf54ec9f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-8900000000-f47c4f9480612fdbc962View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-3900000000-8c82418f7b35a97fb9b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-19b62da79866318c52ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-64b046d21bdcbb8d5923View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-e07b937b6867d1f62293View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-87ab853583aab2973cfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-28814246b728a51e761cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-cfe7e406be2172e94fbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0910000000-478a8345915bc15d85b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-c930c47ecbe6975a00fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-fa6be0f9ce4ee4c30738View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-3425ee9829935182c0d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0fk9-0946231100-3d57d2304dcb33feab3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-5b6dd6fb263ea09289fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-dfe35b3438d19320d8cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-f666ab7e5354bce67a2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03kd-0977452210-046c4b70bd0ec351c41dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-9000000000-2f51e43e530976d63633View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-b9ebb7ebccee1a313888View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0900000000-5379b6fb6ea2313101f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-004i-0900000000-02b2bc83599dc6944f2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00fr-7900000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00fr-7900000000-b7cd48e0aca6a6256968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00fr-7900000000-4e69a6ce7b97433937eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-835751d54af24bd337e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-2d2b5fd7617ccb227bb1View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Avogaro A, Toffolo G, Kiwanuka E, de Kreutzenberg SV, Tessari P, Cobelli C: L-arginine-nitric oxide kinetics in normal and type 2 diabetic subjects: a stable-labelled 15N arginine approach. Diabetes. 2003 Mar;52(3):795-802. Pubmed: 12606522
  • Bauchart-Thevret C, Cui L, Wu G, Burrin DG: Arginine-induced stimulation of protein synthesis and survival in IPEC-J2 cells is mediated by mTOR but not nitric oxide. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E899-909. doi: 10.1152/ajpendo.00068.2010. Epub 2010 Sep 14. Pubmed: 20841502
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. Pubmed: 11113071
  • Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
  • Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  • Haas W, Grabe K, Geis C, Pach T, Stoll K, Fuchs M, Haberl B, Loy C: Recognition and invasion of human skin by Schistosoma mansoni cercariae: the key-role of L-arginine. Parasitology. 2002 Feb;124(Pt 2):153-67. Pubmed: 11860033
  • Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kirkeby HJ, Svane D, Poulsen J, Tottrup A, Forman A, Andersson KE: Role of the L-arginine/nitric oxide pathway in relaxation of isolated human penile cavernous tissue and circumflex veins. Acta Physiol Scand. 1993 Nov;149(3):385-92. Pubmed: 8310843
  • Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. Pubmed: 11952488
  • Linden KC, Wadley GD, Garnham AP, McConell GK: Effect of l-arginine infusion on glucose disposal during exercise in humans. Med Sci Sports Exerc. 2011 Sep;43(9):1626-34. doi: 10.1249/MSS.0b013e318212a317. Pubmed: 21311355
  • Martens-Lobenhoffer J, Bode-Boger SM: Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur J Clin Pharmacol. 2006 Feb;62(Supplement 13):61-68. Pubmed: 16217682
  • Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. Pubmed: 3433275
  • Mori A, Watanabe Y, Fujimoto N: Fluorometrical analysis of guanidino compounds in human cerebrospinal fluid. J Neurochem. 1982 Feb;38(2):448-50. Pubmed: 7108550
  • Noris M, Todeschini M, Cassis P, Pasta F, Cappellini A, Bonazzola S, Macconi D, Maucci R, Porrati F, Benigni A, Picciolo C, Remuzzi G: L-arginine depletion in preeclampsia orients nitric oxide synthase toward oxidant species. Hypertension. 2004 Mar;43(3):614-22. Epub 2004 Jan 26. Pubmed: 14744923
  • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Stothers L, Laher I, Christ GT: A review of the L-arginine - nitric oxide - guanylate cyclase pathway as a mediator of lower urinary tract physiology and symptoms. Can J Urol. 2003 Oct;10(5):1971-80. Pubmed: 14633324
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Meyer, Helmut E.; Swiderek, Kristine; Hoffmann-Posorske, Edeltraut; Korte, Horst; Heilmeyer, Ludwig M. G., Jr. Quantitative determination of phosphoserine by high-performance liquid chromatography as the phenylthiocarbamyl-S-ethylcysteine. Application to
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16467
HMDB IDHMDB00517
Pubchem Compound ID6322
Kegg IDC00062
ChemSpider ID6082
WikipediaL-Arginine
BioCyc IDARG
EcoCyc IDARG
Ligand ExpoGND

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
Gene Name:
hisP
Uniprot ID:
P07109
Molecular weight:
28653
General function:
Involved in arginine N-succinyltransferase activity
Specific function:
Catalyzes the transfer of succinyl-CoA to arginine to produce N(2)-succinylarginine
Gene Name:
astA
Uniprot ID:
P0AE37
Molecular weight:
38456
Reactions
Succinyl-CoA + L-arginine = CoA + N(2)-succinyl-L-arginine.
General function:
Involved in argininosuccinate lyase activity
Specific function:
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
Gene Name:
argH
Uniprot ID:
P11447
Molecular weight:
50318
Reactions
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine.
General function:
Involved in nucleotide binding
Specific function:
ATP + L-arginine + tRNA(Arg) = AMP + diphosphate + L-arginyl-tRNA(Arg)
Gene Name:
argS
Uniprot ID:
P11875
Molecular weight:
64682
Reactions
ATP + L-arginine + tRNA(Arg) = AMP + diphosphate + L-arginyl-tRNA(Arg).
General function:
Involved in catalytic activity
Specific function:
Catalyzes the biosynthesis of agmatine from arginine
Gene Name:
speA
Uniprot ID:
P21170
Molecular weight:
73898
Reactions
L-arginine = agmatine + CO(2).
General function:
Involved in carboxy-lyase activity
Specific function:
ADC can be found in two forms:biodegradative and biosynthetic. The biodegradative form may play a role in regulating pH by consuming proteins
Gene Name:
adiA
Uniprot ID:
P28629
Molecular weight:
84425
Reactions
L-arginine = agmatine + CO(2).
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport
Gene Name:
artI
Uniprot ID:
P30859
Molecular weight:
26929
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Binds L-arginine with high affinity
Gene Name:
artJ
Uniprot ID:
P30860
Molecular weight:
26829
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
artQ
Uniprot ID:
P0AE34
Molecular weight:
26217
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
artM
Uniprot ID:
P0AE30
Molecular weight:
24914
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisM
Uniprot ID:
P0AEU3
Molecular weight:
26870
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisQ
Uniprot ID:
P52094
Molecular weight:
24649
General function:
Involved in transporter activity
Specific function:
This periplasmic binding protein is involved in an arginine transport system. ArgT and histidine-binding protein J (hisJ) interact with a common membrane-bound receptor, hisP
Gene Name:
argT
Uniprot ID:
P09551
Molecular weight:
27991
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for energy coupling to the transport system
Gene Name:
artP
Uniprot ID:
P0AAF6
Molecular weight:
27022

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
Gene Name:
hisP
Uniprot ID:
P07109
Molecular weight:
28653
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport
Gene Name:
artI
Uniprot ID:
P30859
Molecular weight:
26929
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Binds L-arginine with high affinity
Gene Name:
artJ
Uniprot ID:
P30860
Molecular weight:
26829
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
artM
Uniprot ID:
P0AE32
Molecular weight:
24914
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
artQ
Uniprot ID:
P0AE34
Molecular weight:
26217
General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
artM
Uniprot ID:
P0AE30
Molecular weight:
24914
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisM
Uniprot ID:
P0AEU3
Molecular weight:
26870
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisQ
Uniprot ID:
P52094
Molecular weight:
24649
General function:
Involved in transporter activity
Specific function:
This periplasmic binding protein is involved in an arginine transport system. ArgT and histidine-binding protein J (hisJ) interact with a common membrane-bound receptor, hisP
Gene Name:
argT
Uniprot ID:
P09551
Molecular weight:
27991
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in amino acid transmembrane transporter activity
Specific function:
Catalyzes an electroneutral exchange between arginine and ornithine to allow high-efficiency energy conversion in the arginine deiminase pathway
Gene Name:
ydgI
Uniprot ID:
P0AAE5
Molecular weight:
49501
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex ArtPIQMJ involved in arginine transport. Probably responsible for energy coupling to the transport system
Gene Name:
artP
Uniprot ID:
P0AAF6
Molecular weight:
27022
General function:
Involved in amino acid transmembrane transporter activity
Specific function:
Major component of the acid-resistance (AR) system allowing enteric pathogens to survive the acidic environment in the stomach. Exchanges extracellular arginine for its intracellular decarboxylation product agmatine (Agm) thereby expelling intracellular protons
Gene Name:
adiC
Uniprot ID:
P60061
Molecular weight:
46842
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in amino acid transport
Specific function:
Involved in the export of arginine. Important to control the intracellular level of arginine and the correct balance between arginine and lysine. May also be involved in the export of canavanine (a plant-derived antimetabolite)
Gene Name:
argO
Uniprot ID:
P11667
Molecular weight:
23175
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368