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DL-PROPARGYLGLYCINE

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DL-PROPARGYLGLYCINE Basic information

Product Name:
DL-PROPARGYLGLYCINE
Synonyms:
  • H-PROPARGYL-DL-GLYCINE
  • H-PROPARGYL-DL-GLY-OH
  • H-DL-PRA-OH
  • H-DL-GLY(PROPARGYL)-OH
  • DL-PROPARGYLGLYCINE
  • DL-PROPARGYL-GLY-OH
  • 2-AMINO-4-PENTYNOIC ACID
  • NSC21940
CAS:
64165-64-6
MF:
C5H7NO2
MW:
113.11
Product Categories:
  • Amino Acids
Mol File:
64165-64-6.mol
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DL-PROPARGYLGLYCINE Chemical Properties

storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 10 mg/ml) or in Water (up tp 10 mg/ml).
form 
Crystalline Powder
color 
White to off-white
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3

MSDS

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DL-PROPARGYLGLYCINE Usage And Synthesis

Description

Propargylglycine (64165-64-6) is an irreversible inhibitor of the hydrogen sulfide biosynthesis enzyme, cystathione-γ-lyase. It inhibits H2S production in rat liver preparations (IC50=55 μM) and inhibits the rise in plasma H2S in rats with hemorrhagic shock2. Propargylglycine reduces inflammation in a rodent carrageenan-induced hindpaw edema model3 and ameliorates gentamycin-induced nephrotoxicity1.

Chemical Properties

White to off-white powder

Uses

Dl-propargylglycine is an inhibitor of hydrogen sulfide (H2S) production.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 3484, 1954 DOI: 10.1021/ja01642a036
Tetrahedron Letters, 22, p. 1787, 1981 DOI: 10.1016/S0040-4039(01)90439-3

Biochem/physiol Actions

DL-Propargylglycine (PAG) is an irreversible inhibitor of the enzyme cystathionine γ-lyase (GCL), a key enzyme involved in glutathione synthesis and the metabolic transsulfuration pathway which regulates homocysteine concentration and mediates cysteine synthesis. Treatment of animal disease models with PAG was shown to alleviate symptoms of diseases that impair the formation or action of hydrogen sulfide (H2S).

References

1) Dam et al. (2012), Inhibition of cystathione gamma-lyase and the biosynthesis of endogenous hydrogen sulphide ameliorates gentamicin-induced nephrotoxicity; Eur. J. Pharmacol., 685 165 2) Mok et al. (2004), Role of hydrogen sulphide in haemorrhagic shock in the rat: protective effect of inhibitors of hydrogen sulphide biosynthesis; Br. J. Pharmacol., 143 881 3) Bhatia et al. (2005),Hydrogen sulphide is a mediator of carrageenan-induced hindpaw edema in the rat; Br. J. Pharmacol., 145 141

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