slightly soluble in ethanol insoluble in ethyl ether
log P
−1.652
Acidity (pKa)
2.18 (carboxyl), 9.09 (amino), 13.8 (guanidino)
Thermochemistry
Heat capacity (C)
232.8 J K−1 mol−1 (at 23.7 °C)
Std molar entropy (S⦵298)
250.6 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)
−624.9–−622.3 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)
−3.7396–−3.7370 MJ mol−1
Pharmacology
ATC code
B05XB01 (WHO) S
Hazards
GHS labelling:
Pictograms
Signal word
Warning
Hazard statements
H319
Precautionary statements
P305+P351+P338
Lethal dose or concentration (LD, LC):
LD50 (median dose)
5110 mg/kg (rat, oral)
Safety data sheet (SDS)
L-Arginine
Related compounds
Related alkanoic acids
N-Methyl-D-aspartic acid
beta-Methylamino-L-alanine
Guanidinopropionic acid
Theanine
Pantothenic acid
Related compounds
Panthenol
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).
Infobox references
Chemical compound
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]
^"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.
^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.
^Ignarro LJ (2000-09-13). Nitric Oxide: Biology and Pathobiology. Academic Press. p. 189. ISBN 978-0-08-052503-7.
^"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.
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...
In enzymology, an arginine deiminase (EC 3.5.3.6) is an enzyme that catalyzes the chemical reaction L-arginine + H2O ⇌{\displaystyle \rightleftharpoons...
In enzymology, arginine kinase (EC 2.7.3.3) is an enzyme that catalyzes the chemical reaction ATP + L-arginine ⇌ {\displaystyle \rightleftharpoons } ADP...
Human vasopressin, also called antidiuretic hormone (ADH), arginine vasopressin (AVP) or argipressin, is a hormone synthesized from the AVP gene as a peptide...
medical use in 1988. Perindopril is taken in the form of perindopril arginine (with arginine, trade names include Coversyl, Coversum) or perindopril erbumine...
Arginine carboxypeptidase may refer to: Lysine carboxypeptidase, an enzyme Carboxypeptidase U, an enzyme This set index page lists enzyme articles associated...
an arginine racemase (EC 5.1.1.9) is an enzyme that catalyzes the chemical reaction L-arginine ⇌{\displaystyle \rightleftharpoons } D-arginine Hence...
Argininosuccinate undergoes cleavage by argininosuccinase to form arginine and fumarate. Arginine is cleaved by arginase to form urea and ornithine. The ornithine...
Citrullination or deimination is the conversion of the amino acid arginine in a protein into the amino acid citrulline. Citrulline is not one of the 20...
Central diabetes insipidus, recently renamed arginine vasopressin deficiency (AVP-D), is a form of diabetes insipidus that is due to a lack of vasopressin...
In molecular biology, an arginine finger is an amino acid residue of some enzymes. Arginine fingers are often found in the protein superfamily of AAA+...
family of enzymes catalyzing the production of nitric oxide (NO) from L-arginine. NO is an important cellular signaling molecule. It helps modulate vascular...
takes place on arginine or lysine amino acid residues in the protein sequence. Arginine can be methylated once (monomethylated arginine) or twice, with...
process by which proteins containing methylated arginine are broken down and removed from the body. Arginine (Arg) is a non-essential amino acid and one of...
Nitroarginine, or Nω-nitro-l-arginine, also known as L-NOARG, is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase...
Protein Arginine Phosphatase (PAPs), also known as Phosphoarginine Phosphatase, is an enzyme that catalyzes the dephosphorylation of phosphoarginine residues...
such as arginine methylation and lysine methylation do not require pre-processing. Arginine can be methylated once (monomethylated arginine) or twice...
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