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Topic summary

Arginine

Arginine
Names IUPAC names
Arginine
Systematic IUPAC name
2-Amino-5-guanidinopentanoic acid
Identifiers
3D model (JSmol)
1725411, 1725412 D, 1725413 LChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.738EC Number
  • L: 230-571-3
364938 D
KEGG
MeSHArginine
RTECS number
  • L: CF1934200 L
UNII
  • 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
    Key: ODKSFYDXXFIFQN-BYPYZUCNSA-N
  • D/L: Key: ODKSFYDXXFIFQN-UHFFFAOYSA-N
  • D: Key: ODKSFYDXXFIFQN-SCSAIBSYSA-N
  • L: C(C[C@@H](C(=O)O)N)CNC(=N)N
  • D/L: C(CC(C(=O)O)N)CNC(=N)N
  • D: C(C[C@H](C(=O)O)N)CNC(=N)N
  • L HCl: [Cl-].NC(CCCNC(N)=[NH2+])C([O-])=O
  • L Zwitterion: NC(CCCNC(N)=[NH2+])C([O-])=O
Properties C6H14N4O2Molar mass174.204 g·mol Appearance White crystals OdorOdourless Melting point260 °C; 500 °F; 533 K Boiling point368 °C (694 °F; 641 K) 14.87 g/100 mL (20 °C) Solubilityslightly soluble in ethanol
insoluble in ethyl etherlog P−1.652 Acidity (pKa) 2.18 (carboxyl), 9.09 (amino), 13.8 (guanidino) Thermochemistry 232.8 J K mol (at 23.7 °C) 250.6 J K mol −624.9–−622.3 kJ mol −3.7396–−3.7370 MJ mol Pharmacology B05XB01 (WHO) SHazards GHS labelling: WarningH319P305+P351+P338Lethal dose or concentration (LD, LC): 5110 mg/kg (rat, oral) Safety data sheet (SDS) L-ArginineRelated compounds
Related alkanoic acids
Related compounds
Supplementary data page Arginine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2) and both the amino and guanidino groups are protonated, resulting in a cation. Only the L-arginine (symbol Arg or R) enantiomer is found naturally. Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the precursor for the biosynthesis of nitric oxide. Like all amino acids, it is a white, water-soluble solid.

The one-letter symbol R was assigned to arginine for its phonetic similarity in English.

Wikipedia source