D(-)-Arginine CAS 157-06-2

Introduction：Basic information about D(-)-Arginine CAS 157-06-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

D(-)-Arginine Basic information

• Product Name: D(-)-Arginine
• Synonyms: (2R)-2-ammonio-5-(diaminomethylideneammonio)pentanoate;R-(-)-ARGININE;(R)-2-AMINO-5-GUANIDINOPENTANOIC ACID;RARECHEM AB PP 1748;D-ARG;D-(-)-ARGININE;D-ARGININE;D-2-AMINO-5-GUANIDINOVALERIC ACID
• CAS: 157-06-2
• MF: C6H14N4O2
• MW: 174.2
• EINECS: 205-866-5
• Product Categories: amino;Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;PROTECTED AMINO ACID & PEPTIDES;Amino Acids Derivatives;chiral
• Mol File: 157-06-2.mol

D(-)-Arginine Chemical Properties

• Melting point: 226 °C (dec.) (lit.)
• alpha: -28.5 º (c=8, 6 N HCl)
• Boiling point: 305.18°C (rough estimate)
• density: 1.2297 (rough estimate)
• refractive index: -23 ° (C=8, 6mol/L HCl)
• storage temp.: Keep in dark place,Inert atmosphere,Room temperature
• solubility: Aqueous Acid (Slightly), Water (Slightly)
• pka: 2.49±0.24(Predicted)
• form: Solid
• color: White to Off-White
• Water Solubility: SOLUBLE
• Sensitive: Air Sensitive
• BRN: 1725412
• Major Application: peptide synthesis
• 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-/m1/s1
• InChIKey: ODKSFYDXXFIFQN-SCSAIBSYSA-N
• SMILES: N[C@H](CCCNC(N)=N)C(O)=O
• LogP: -0.999 (est)
• CAS DataBase Reference: 157-06-2(CAS DataBase Reference)
• EPA Substance Registry System: D-Arginine (157-06-2)

Safety Information

• Hazard Codes: Xi,Xn
• Risk Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CF1934220
• F: 9
• TSCA: TSCA listed
• HazardClass: IRRITANT
• HS Code: 29252000
• Storage Class: 11 - Combustible Solids

D(-)-Arginine Usage And Synthesis

Description

D-arginine is the D-form of arginine, which is a kind of amino acids. It can be reacted with hydrogen peroxide for non-enzymatic synthesis of nitric oxide. It has certain pharmacological activities. For example, its derivative, 1-deamino-8-D-arginine vasopressin is useful for the management of haemophilia and von Willebrand’s disease. It also has the potential to inhibit the proliferation of certain cancer cells. In biological research, D-arginine is frequently used in the studies of L-arginine/nitric oxide pathway as an inactive form of L-arginine.

Chemical Properties

white to light yellow crystal powde

Uses

Arginine is an essential amino acid found in food and plant sources, and many biological systems.
D-Arginine is extensively used in studies on L-arginine/nitric oxide pathway as an inactive form of L-arginine, even in man.
D-Arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. D-Arginine specifically can inhibit arginine decarboxylase enzymes and also functions as a metabolite.

Uses

1-Deamino-8-D-arginine vasopressin makes a new pharmacological approach to the management of haemophilia and von Willebrand's disease. A novel nonenzymatic pathway for the generation of nitric oxide is by the reaction of hydrogen peroxide and d- or l-arginine.

Definition

ChEBI: D-arginine is a D-alpha-amino acid that is the D-isomer of arginine. It has a role as an EC 4.1.1.19 (arginine decarboxylase) inhibitor and a mouse metabolite. It is a D-alpha-amino acid and an arginine. It is a conjugate base of a D-argininium(1+). It is a conjugate acid of a D-argininate. It is an enantiomer of a L-arginine.

in vivo

D-arginine (1 mg/kg, i.v., caudal veins, every two days) sensitize osteosarcoma to radiotherapy in a mouse model of subcutaneous osteosarcoma^[3].
The number of D-arginine residues in cell-penetrating peptides (i.v.) significantly affects their cellular uptake behavior and systemic toxicity in mice^[4].
D-Arginine (700 mg/kg, i.p.) displays central stimulant properties and increases spontaneous motor activity in mice^[5].
D-arginine (i.p.) shows a light toxicity order (LD50: 2800 mg/kg) in mice^[5].
D-arginine (1400 mg/kg, i.p.) protects against Pentylenetetrazole-induced convulsions in mice^[5].
D-arginine (1000 mg/kg, p.o., 16 weeks) significantly alters various enzymes and metabolites in the arginine metabolic pathways in male SD rats^[6].
D-arginine (1000 mg/kg, s.c., coadministered with L-arginine) blocks antinociception elicited by L-arginine (HY-N0455) in mice with Carrageenin-induced hyperalgesia^[7].
D-arginine (20 mg/kg, s.c.) does not significantly alter the percentage of antinociception in mice^[8].

• Animal Model: Female BALB/c mice (anesthetized by intraperitoneal injection of 3% pentobarbital sodium; K7M2 cells were injected subcutaneously; X-ray irradiation)^[2]
• Dosage: 1 mg/kg
• Administration: Intravenous injection (i.v.), caudal veins, every two days
• Result: Inhibited tumor volume (20 days).

IC 50

Human Endogenous Metabolite

References

https://www.alfa.com/zh-cn/catalog/A16137/
Iannucci, N. B., et al. "Antiproliferative effect of 1-deamino-8-D-arginine vasopressin analogs on human breast cancer cells." Future Medicinal Chemistry 3.16(2011):1987-1993.
Ripoll, Giselle, et al. "Angiostatic activity of 1-Deamino-8-D-Arginine vasopressin and novel peptide analogues in breast cancer cells." Cancer Research 68(2008).
Navarro, Eduardo, et al. "Toxicological and Pharmacological Effects of D-Arginine." Basic & Clinical Pharmacology & Toxicology97.3(2005):149-154.

D(-)-Arginine Preparation Products And Raw materials

• Raw materials: D-Ornithine monohydrochloride