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L-arginine

Arginine
Skeletal formula of arginine
Arginine-3D-balls-by-AHRLS-2012.png
Names
Other names
2-Amino-5-guanidinopentanoic acid
Identifiers
7200-25-1 N
157-06-2 R N
74-79-3 S N
3D model (Jmol) Interactive image
Interactive image
3DMet B01331
1725411, 1725412 R, 1725413 S
ChEBI CHEBI:29016 YesY
ChEMBL ChEMBL212301 N
ChEMBL1485 N
ChemSpider 227 YesY
64224 R N
6082 S N
DrugBank DB00125 N
ECHA InfoCard 100.000.738
EC Number 230-571-3
364938 R
721
KEGG C02385 N
MeSH Arginine
PubChem 232
71070 R
6322 S
RTECS number CF1934200 S
UNII 94ZLA3W45F YesY
Properties
C6H14N4O2
Molar mass 174.20 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) 12.488
Basicity (pKb) 1.509
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
Safety data sheet See: data page
sigma-aldrich
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H319
P305+351+338
Irritant Xi
R-phrases R36
S-phrases S26
Lethal dose or concentration (LD, LC):
LD50 (median dose)
5110 mg/kg (rat, oral)
Related compounds
Related alkanoic acids
Related compounds
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Arginine (abbreviated as Arg or R) encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG is an α-amino acid that is used in the biosynthesis of proteins.

Arginine is classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Preterm infants are unable to synthesize or create arginine internally, making the amino acid nutritionally essential for them. Most healthy people do not need to supplement with arginine because their body produces sufficient amounts.

Arginine was first isolated from a lupin seedling extract in 1886 by the German chemist Ernst Schultze. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO form under biological conditions), and a side chain of a 3-carbon aliphatic straight chain capped by a complex guanidinium, classifying it as a charged (at physiological pH), aliphatic amino acid.

A conditionally essential amino acid is one that may be required depending on the health status or life cycle of the individual. Arginine is one such conditionally essential amino acid. The biosynthetic pathway, however, does not produce sufficient arginine, and some must still be consumed through diet. Individuals with poor nutrition or certain physical conditions may be advised to increase their intake of foods containing arginine. Arginine is found in a wide variety of foods, including:

Arginine is synthesized from citrulline in arginine and proline metabolism by the sequential action of the cytosolic enzymes argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL). In terms of energy, this is costly, as the synthesis of each molecule of argininosuccinate requires hydrolysis of adenosine triphosphate (ATP) to adenosine monophosphate (AMP), i.e., two ATP equivalents. In essence, taking an excess of arginine gives more energy by saving ATPs that can be used elsewhere.


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Wikipedia

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