D(-)-Arginine
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)
- form
- Solid
- pka
- 2.49±0.24(Predicted)
- color
- White to Off-White
- Water Solubility
- SOLUBLE
- Sensitive
- Air Sensitive
- BRN
- 1725412
- InChIKey
- ODKSFYDXXFIFQN-SCSAIBSYSA-N
- 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
- Yes
- HazardClass
- IRRITANT
- HS Code
- 29252000
MSDS
- Language:English Provider:D(-)-Arginine
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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.
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