D(-)-Arginine
Synonym(s):(R)-2-Amino-5-guanidinopentanoic acid
- CAS NO.:157-06-2
- Empirical Formula: C6H14N4O2
- Molecular Weight: 174.2
- MDL number: MFCD00063116
- EINECS: 205-866-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-06-03 14:46:32
What is D(-)-Arginine?
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
The Uses of D(-)-Arginine
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.
The Uses of D(-)-Arginine
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: A D-alpha-amino acid that is the D-isomer of arginine.
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.
Properties of D(-)-Arginine
Melting point: | 226 °C (dec.) (lit.) |
Boiling point: | 305.18°C (rough estimate) |
alpha | -28.5 º (c=8, 6 N HCl) |
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 |
CAS DataBase Reference | 157-06-2(CAS DataBase Reference) |
EPA Substance Registry System | D-Arginine (157-06-2) |
Safety information for D(-)-Arginine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for D(-)-Arginine
InChIKey | ODKSFYDXXFIFQN-SCSAIBSYSA-N |
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