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L-(+)-Arginine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

L-Arginine is the nitrogen donor for synthesis of nitric oxide, a potent vasodilator that is deficient during times of sickle cell crisis. It is an α-amino acid and was first isolated in 1886. It is associated with a decrease in cardiac index while stroke index is maintained in patients with severe sepsis.

Category

L-Amino Acids

Catalog number

BAT-014316

CAS number

74-79-3

Molecular Formula

C6H14N4O2

Molecular Weight

174.20

IUPAC Name

(2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid

Synonyms

L-Arginine; Arginine, L-; (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid; L-Arg; L-Norvaline, 5-[(aminoiminomethyl)amino]-; L-Ornithine, N5-(aminoiminomethyl)-; L-α-Amino-δ-guanidinovaleric acid; A 0526; Arginine; L-arginine C Grade; NSC 206269; Pentanoic acid, 2-amino-5-[(aminoiminomethyl)amino]-, (S)-

Related CAS

1119-34-2 (hydrochloride) 142-49-4 (Deleted CAS) 7004-12-8 (Deleted CAS) 154605-63-7 (Deleted CAS) 154605-67-1 (Deleted CAS) 667422-95-9 (Deleted CAS) 1332377-47-5 (Deleted CAS)

Appearance

White or almost white crystalline powder or colorless crystals, hygroscopic

Purity

>98%

Density

1.10 g/cm3

Melting Point

244°C

Boiling Point

367.6±52.0°C at 760 Torr

Storage

Store at RT

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

InChI Key

ODKSFYDXXFIFQN-BYPYZUCNSA-N

Canonical SMILES

C(CC(C(=O)O)N)CN=C(N)N

L-(+)-Arginine is an essential amino acid that plays a critical role in several physiological processes within the human body. It is commonly found in dietary proteins and can also be synthesized in the body. L-(+)-Arginine is a precursor to nitric oxide, a molecule that facilitates vasodilation and helps improve blood flow. This amino acid is vital for cellular functions, wound healing, and immune responses, making it significant for both health and medical research. In commercial forms, L-(+)-Arginine is often used as a dietary supplement for athletes and individuals seeking to support cardiovascular health.

One key industrial application of L-(+)-Arginine is in the pharmaceutical sector. It is used in the formulation of medications intended to promote cardiovascular health by enhancing nitric oxide production, thus improving vasodilation and circulation. This property makes it beneficial in the treatment of conditions like hypertension, angina, and erectile dysfunction. Additionally, L-(+)-Arginine is frequently incorporated into formulations aimed at immune support and wound healing due to its role in promoting cellular repair and growth.

Another significant application is within the sports nutrition industry. L-(+)-Arginine is commonly included in pre-workout and post-workout supplements designed to boost athletic performance. By increasing nitric oxide levels, it helps improve blood flow to muscles, thereby enhancing exercise endurance and reducing recovery times. The amino acid’s potential to stimulate protein synthesis also aids in muscle growth and repair, making it a popular choice among bodybuilders and athletes.

The cosmetic industry also utilizes L-(+)-Arginine in various skincare formulations. Its role in collagen production and circulation improvement makes it an ideal ingredient for products aimed at anti-aging and skin rejuvenation. L-(+)-Arginine can help enhance skin elasticity, reduce the appearance of wrinkles, and aid in the healing of damaged skin. Moreover, its moisturizing properties make it suitable for use in creams and serums intended to hydrate and nourish the skin.

Lastly, L-(+)-Arginine has applications in agriculture, particularly in animal feed. It serves as a dietary supplement to ensure that livestock receives essential nutrients necessary for growth and health. Its inclusion in feed formulations can enhance the overall immune response of animals, improving their resistance to diseases. Furthermore, L-(+)-Arginine supports reproductive health and development in livestock, contributing to better productivity and yield. This makes it an invaluable addition to animal husbandry practices aimed at optimizing livestock health and performance.

1.Evidence for N-Terminal Myristoylation of Tetrahymena Arginine Kinase Using Peptide Mass Fingerprinting Analysis.

Motomura S1, Suzuki T2. Protein J. 2016 Apr 30. [Epub ahead of print]

In this study, we confirmed N-terminal myristoylation of Tetrahymena pyriformis arginine kinase (AK1) by identifying a myristoylation signal sequence at the N-terminus. A sufficient amount of modified enzyme was synthesized using an insect cell-free protein synthesis system that contains all of the elements necessary for post-transcriptional modification by fatty acids. Subsequent peptide mass fingerprinting (PMF) analyses were performed after digestion with trypsin. The PMF data covered 39 % (143 residues) of internal peptides. The target N-myristoylated peptide had a theoretical mass of 832.4477 and was clearly observed with an experimental mass (m/z-H+) of 832.4747. The difference between the two masses was 0.0271, supporting the accuracy of identification and indicating that the synthesized T. pyriformis AK1 is myristoylated. The fixed specimens of T. pyriformis were reacted with an anti-AK1 peptide antibody followed by a secondary antibody with a fluorescent chromophore and were observed using immunofluorescence microscope.

2.Gonadotropin-releasing hormone agonist prevents L-arginine induced immune dysfunction independent of gonadal steroids: Relates with a decline in elevated thymus and brain nitric oxide levels.

Ullewar MP1, Umathe SN2. Nitric Oxide. 2016 Apr 26. pii: S1089-8603(16)30030-1. doi: 10.1016/j.niox.2016.04.009. [Epub ahead of print]

The present study was carried out to find out the effect of leuprolide, a gonadotropin-releasing hormone (GnRH) receptor agonist, on l-arginine induced immunosuppression, and relates with brain and thymus levels of nitric oxide (NO). Further, the effect of leuprolide was studied in sham operated, ovariectomized and castrated mice to understand the role of sex steroids in l-arginine induced immunosuppression. Treatment with l-arginine (250, 500, 1000 mg/kg/i.p. for 7 days) increased brain and thymus levels of NO; measured by using 'NO Measuring Instrument' (Innovative Instruments Inc., USA) in dose dependent manner. It also decreased cellularity, relative weight of thymus, DNA fragmentation, humoral, and cell mediated immunity response to sheep RBC. Prior treatment of leuprolide (100μg/mouse, s.c. for 7 days) prevented l-arginine induced rise in brain and thymus tissue levels of NO as well as the changes in immunological parameters. The protective effect of leuprolide against l-arginine induced immunosuppression and rise in brain and tissue nitric oxide levels was even evident in ovariectomized and castrated mice, suggesting that the observed effect of leuprolide is independent of sex steroids, and correlated with its ability to prevent l-arginine induced rise in CNS and peripheral immune tissue levels of NO.

3.Reduced arginine availability and nitric oxide synthesis in cancer is related to impaired endogenous arginine synthesis.

Engelen MP1, Safar AM2, Bartter T3, Koeman F4, Deutz NE5. Clin Sci (Lond). 2016 Apr 7. pii: CS20160233. [Epub ahead of print]

Reduced plasma arginine (ARG) concentrations are found in various types of cancer. ARG and its product nitric oxide (NO) are important mediators in the immune function and the defense against tumor cells. It remains unclear whether the diminished systemic ARG availability in cancer is related to insufficient endogenous ARG synthesis, negatively affecting NO synthesis, and whether a dietary amino acid mixture is able to restore this. In 13 patients with advanced non-small cell lung cancer (NSCLC) and 11 healthy controls, whole body ARG and CIT rates of appearance were measured by stable isotope methodology before and after intake of a mixture of amino acids as present in whey protein. The conversions of CIT to ARG (indicator of de novo ARG synthesis) and ARG to CIT (marker of NO synthesis), and ARG clearance (reflecting ARG disposal capacity) were calculated. Plasma isotopic enrichments and amino acid concentrations were measured by LC-MS/MS.

4.Hepatocyte growth factor, hepatocyte growth factor activator and arginine in a rat fulminant colitis model.

Zwintscher NP1, Shah PM2, Salgar SK3, Newton CR4, Maykel JA5, Samy A6, Jabir M6, Steele SR6. Ann Med Surg (Lond). 2016 Apr 5;7:97-103. doi: 10.1016/j.amsu.2016.03.039. eCollection 2016.

INTRODUCTION: Dextran sodium sulfate (DSS) is commonly used to induce a murine fulminant colitis model. Hepatocyte growth factor (HGF) has been shown to decrease the symptoms of inflammatory bowel disease (IBD) but the effect of its activator, HGFA, is not well characterized. Arginine reduces effects of oxidative stress but its effect on IBD is not well known. The primary aim is to determine whether HGF and HGFA, or arginine will decrease IBD symptoms such as pain and diarrhea in a DSS-induced fulminant colitis murine model.