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HomeProduct name listD(-)-Arginine

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
D(-)-Arginine Structural

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)
ghs
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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