Arginine

Arginine
Skeletal formula of arginine
Skeletal formula of arginine
Names
IUPAC names
Arginine
Other names
2-Amino-5-guanidinopentanoic acid
Identifiers
3D model (JSmol)
3DMet
1725411, 1725412 D, 1725413 L
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.738 Edit this at Wikidata
EC Number
  • L: 230-571-3
364938 D
KEGG
MeSH Arginine
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 checkY
    Key: ODKSFYDXXFIFQN-BYPYZUCNSA-N checkY
  • 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
C6H14N4O2
Molar mass 174.204 g·mol−1
Appearance White crystals
Odor Odourless
Melting point 260 °C; 500 °F; 533 K
Boiling point 368 °C (694 °F; 641 K)
14.87 g/100 mL (20 °C)
Solubility slightly soluble in ethanol
insoluble in ethyl ether
log P −1.652
Acidity (pKa) 2.18 (carboxyl), 9.09 (amino), 13.8 (guanidino)
Thermochemistry
232.8 J K−1 mol−1 (at 23.7 °C)
250.6 J K−1 mol−1
−624.9–−622.3 kJ mol−1
−3.7396–−3.7370 MJ mol−1
Pharmacology
B05XB01 (WHO) S
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
P305+P351+P338
Lethal dose or concentration (LD, LC):
5110 mg/kg (rat, oral)
Safety data sheet (SDS) L-Arginine
Related 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.[1] Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG.[2] The guanidine group in arginine is the precursor for the biosynthesis of nitric oxide.[3] Like all amino acids, it is a white, water-soluble solid.

The one-letter symbol R was assigned to arginine for its phonetic similarity.[4]

  1. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
  2. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Archived from the original on 29 May 2007. Retrieved 2007-05-17.
  3. ^ Ignarro LJ (2000-09-13). Nitric Oxide: Biology and Pathobiology. Academic Press. p. 189. ISBN 978-0-08-052503-7.
  4. ^ "IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6.