L-Arginine (ECMDB00517) (M2MDB000146)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:27:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:08 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| 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 |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | L-alpha-amino acids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 222 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| 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 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 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 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 L-Arginine + tRNA(Arg) + Adenosine triphosphate + Hydrogen ion > Pyrophosphate + Adenosine monophosphate + L-arginyl-tRNA(Arg) L-Arginine + Adenosine triphosphate + Water > L-Arginine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP L-Arginine + Adenosine triphosphate + Water > L-Arginine + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine More...L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide L-Arginine + Adenosine triphosphate + tRNA(Arg) <> Adenosine monophosphate + L-Arginyl-tRNA(Arg) + Pyrophosphate Argininosuccinic acid <> L-Arginine + Fumaric acid L-Arginine + Hydrogen ion <> Agmatine + Carbon dioxide L-Arginine + Succinyl-CoA <> Coenzyme A + Hydrogen ion + N2-Succinyl-L-arginine L-Arginine + Adenosine triphosphate + tRNA(Arg) <> Adenosine monophosphate + L-Arginyl-tRNA(Arg) + Pyrophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| 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) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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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