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Arginine

Catalog Number
ACM74793
CAS
74-79-3
Structure
IUPAC Name
(2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid
Synonyms
L-Arginine
Molecular Weight
174.2
Molecular Formula
C6H14N4O2
Canonical SMILES
C(C[C@@H](C(=O)O)N)CN=C(N)N
InChI
ODKSFYDXXFIFQN-BYPYZUCNSA-N
InChI Key
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
Boiling Point
305°C
Melting Point
222 °C (dec.) (lit.)
Purity
99%+
Density
1.23g/ml
Appearance
white, crystalline powder that is water-soluble and odorless
Application
1. Helps improve blood flow and circulation
2. Enhances athletic performance and endurance
3. Boosts immune system function
4. Supports wound healing and tissue repair
5. May aid in erectile dysfunction by improving blood flow to the genitals
6. Assists in reducing high blood pressure
7. Can act as a natural remedy for migraines and headaches by dilating blood vessels
8. May have anti-aging effects due to its role in collagen production.
Active Content
95%
pH
10.5-12.0 (0.5M, H2O, 25°C)
Physical State
Solid
Typical Applications
Perfume
Spec Sheet
Case Study

Preparation of Graphitic Carbon Nitride Supported l-Arginine as a Highly Efficient and Recyclable Catalyst

Preparation of Graphitic Carbon Nitride Supported l-Arginine as a Highly Efficient and Recyclable Catalyst Ghafuri, Hossein, et al. Scientific reports 11.1 (2021): 19792.

In this study, a graphitic carbon nitride supported l-arginine (g-C₃N₄@l-arginine) nanocatalyst was synthesized. The novel g-C₃N₄@l-arginine nanocatalyst exhibited high thermal stability, ease of separation from the reaction medium, applicability to various multi-component reactions, and acceptable reusability.
Experimental Procedure: Graphitic carbon nitride (g-C₃N₄) nanosheets (1.0 g) were dispersed in anhydrous toluene (20.0 mL). Then, 1,3-dibromopropane (2.0 mL) was added, and the reaction mixture was refluxed under a nitrogen atmosphere for 24 hours. Finally, the product was filtered, washed with ethyl acetate, and dried at room temperature. The obtained product was dissolved in a mixture of water and methanol (1:1), followed by the addition of l-arginine (1 mmol), K₂CO₃ (1.0 mmol), and NaI (1.0 mmol). The solution was stirred at room temperature for 24 hours. The reaction mixture was then washed with water and methanol and dried at room temperature.

Synthesis of Novel Light-Emitting Nanocomposites Based on Arginine

Synthesis of Novel Light-Emitting Nanocomposites Based on Arginine Aslani, Robab, and Hassan Namazi. Journal of Industrial and Engineering Chemistry 112 (2022): 335-347.

This study aims to synthesize a novel light-emitting nanocomposite based on an arginine-derived dendritic polymer for drug delivery applications through a simple method. A new dendritic polymer (HBPAC) was synthesized by copolymerizing citric acid (as an A3-type monomer) and L-arginine (as an AB2-type monomer), which was then complexed with glucose-derived quantum dots (GluQD) to form the HBPAC-GluQD nanocarrier.
Synthesis of Dendritic Poly(L-arginine Citraconamide) (HBPAC): In a 100 mL round-bottom flask, anhydrous citric acid (1 g, 0.781 mmol), L-arginine (1.37 mmol), LiCl (0.39 g), and 15 mL of DMSO solvent were heated under an argon atmosphere for 48 hours while stirring with a mechanical stirrer. The reaction mixture was then dialyzed against deionized water at 25 °C for 48 hours using a dialysis tube with a cutoff value of 2 kDa. Afterward, the prepared HBPAC was collected using a rotary evaporator under vacuum at 60 °C and dried in an oven at 55 °C.
Synthesis of HBPAC-GluQD Nanocomposite: A mixture of 0.2 g HBPAC copolymer, 0.11 g D(+)-glucose (0.60 mmol), and 35 mL deionized water was transferred into a stainless steel autoclave with a PTFE liner and heated at 180 °C for 6 hours. The resulting nanocarriers were then separated by centrifugation, washed several times with distilled water, and dried at 35 °C.

L-Arginine Induces Antioxidant Responses to Prevent Oxidative Stress

L-Arginine Induces Antioxidant Responses to Prevent Oxidative Stress Liang, Mingcai, et al. Food and chemical toxicology 115 (2018): 315-328.

L-arginine induces antioxidant responses to prevent oxidative stress by stimulating glutathione synthesis and activating the Nrf2 pathway.
L-arginine is a conditionally essential amino acid. To investigate the effect of L-arginine on the activation of endogenous antioxidant defenses, male Wistar rats were orally administered different doses of L-arginine at 25, 50, and 100 mg/100 g body weight daily. After 7 and 14 days of feeding, the antioxidant capacity and glutathione (GSH) levels in plasma and liver were significantly enhanced with increasing L-arginine intake, while oxidative stress was effectively suppressed by L-arginine treatment. After 14 days of feeding, the mRNA levels and protein expression of Keap1 and Cul3 gradually decreased with increasing L-arginine intake, leading to the activation of nuclear factor Nrf2. Following Nrf2 activation, the expression of antioxidant response element (ARE)-dependent genes and proteins (GCLC, GCLM, GS, GR, GST, GPx, CAT, SOD, NQO1, HO-1) was upregulated due to L-arginine feeding, indicating an increase in antioxidant capacity with greater L-arginine consumption. This study suggests that L-arginine supplementation stimulates GSH synthesis and activates the Nrf2 pathway, thereby upregulating ARE-driven antioxidant expression via the Nrf2-Keap1 pathway. The results indicate that the availability of L-arginine is a key factor in inhibiting oxidative stress and inducing endogenous antioxidant responses.

Custom Q&A

How is arginine traditionally obtained?

Arginine is traditionally obtained by hydrolysis of various cheap sources of protein, such as gelatin.

How is arginine commercially produced?

Arginine can be commercially produced by fermentation, using glucose as a carbon source.

How is arginine synthesized in the body?

Arginine is synthesized from citrulline in the urea cycle by the action of argininosuccinate synthetase and argininosuccinate lyase enzymes.

Why is arginine synthesis considered an energetically costly process?

Arginine synthesis is considered energetically costly because for each molecule of argininosuccinate synthesized, one molecule of ATP is hydrolyzed, consuming two ATP equivalents.

How is arginine recycled in the body?

Citrulline, a byproduct of nitric oxide production, can be recycled to arginine in a pathway known as the citrulline to nitric oxide (citrulline-NO) or arginine-citrulline pathway.

What functions does arginine play in the body?

Arginine plays a role in cell division, wound healing, removing ammonia from the body, immune function, and the release of hormones. It is also a precursor for the synthesis of nitric oxide, which regulates blood pressure.

Where is arginine typically found in proteins?

Arginine is typically found on the outside of proteins, where the hydrophilic head group can interact with the polar environment.

How is arginine modified in proteins?

Arginine residues in proteins can be deiminated to form citrulline, and can also be methylated by protein methyltransferases.

What are the precursors and products of arginine?

Arginine is a precursor for nitric oxide, urea, ornithine, agmatine, creatine, and polyamines. Asymmetric dimethylarginine (ADMA), a close relative of arginine, inhibits the nitric oxide reaction and is considered a marker for vascular disease.

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