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D-Pyroglutamic acid

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D-Pyroglutamic acid Basic information

Product Name:
D-Pyroglutamic acid
Synonyms:
  • (R)-5-PYRROLIDONE-2-CARBOXYLIC ACID
  • (R)-(+)-5-OXO-2-PYRROLIDINECARBOXYLIC ACID
  • (R)-5-OXO-2-PYRROLIDINECARBOXYLIC ACID
  • (R)-5-OXOPYRROLIDINE-2-CARBOXYLIC ACID
  • (R)-(+)-2-PYRROLIDINONE-5-CARBOXYLIC ACID
  • (R)-2-PYRROLIDINONE-5-CARBOXYLIC ACID
  • (R)-(+)-2-PYRROLIDONE-5-CARBOXYLIC ACID
  • (R)-2-PYRROLIDONE-5-CARBOXYLIC ACID
CAS:
4042-36-8
MF:
C5H7NO3
MW:
129.11
EINECS:
223-735-0
Product Categories:
  • Amino Acids & Derivatives
  • Chiral Reagents
  • Pyroglutamic acid [Pyr, pGu]
  • Amino Acids 13C, 2H, 15N
  • Amino Acids
  • amino acid
  • Amino Acids and Derivatives
  • Heterocycles
  • chiral
  • Biochemistry
  • Biological-modified Amino Acids
  • for Resolution of Bases
  • Optical Resolution
  • Synthetic Organic Chemistry
  • pharmacetical
  • bc0001
Mol File:
4042-36-8.mol
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D-Pyroglutamic acid Chemical Properties

Melting point:
155-162 °C
alpha 
27.5 º (c=10,1N NaOH)
Boiling point:
239.15°C (rough estimate)
Density 
1.3816 (rough estimate)
refractive index 
10 ° (C=5, H2O)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water
form 
Solid
pka
3.48±0.20(Predicted)
color 
Off-White to Light Beige
optical activity
[α]22/D +10°, c = 1.5 in H2O
Water Solubility 
soluble
Merck 
14,8001
BRN 
82133
InChIKey
ODHCTXKNWHHXJC-GSVOUGTGSA-N
CAS DataBase Reference
4042-36-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
HS Code 
29339900

MSDS

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D-Pyroglutamic acid Usage And Synthesis

Description

D-Pyroglutamic acid, also known as 5-oxo-D-proline, is a metabolite of D-glutamate. It is formed from D-glutamate by D-glutamate cyclase. The levels of D-pyroglutamic acid are increased in the urine of patients with nascent metabolic syndrome and the plasma of patients with end-stage renal disease.

Chemical Properties

white to light yellow crystal powder.

Occurrence

D-pyroglutamic acid is formed by the dehydration between the α-NH2 group and the γ-hydroxyl group of glutamic acid to form an intramolecular amide bond; it can also be formed by the loss of an amide group in the glutamine molecule.

Uses

Serves as a building block in the synthesis of diphthamide.

Definition

ChEBI: D-Pyroglutamic acid is the D-enantiomer of 5-oxoproline. It has a role as a metabolite. It is a D-proline derivative and a 5-oxoproline. It is a conjugate acid of a 5-oxo-D-prolinate. It is an enantiomer of a 5-oxo-L-proline.

Biological Activity

D-Pyroglutamic acid (PCA) is a cyclic derivative of glutamic acid, physiologically present in mammalian tissues. It has been shown that PCA releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, PCA significantly shortens the plasma half-life of ethanol during acute intoxication.

Purification Methods

Purify R-pyroglutamic acid by dissolving it in H2O, filtering, passing the filtrate through Dowex 50 (H+ form), washing with H2O, pooling washings, evaporating, removing H2O azeotropically with Me2CO and *C6H6, washing the residue with Et2O and recrystallising from EtOH/pet ether. [Pradeller et al. Collect Czech Chem Commun 42 79, 80 1977, Beilstein 22/6 V 7.]

References

1. Ariyoshi, M., Katane, M., Hamase, K., et al. D-Glutamate is metabolized in the heart mitochondria. Sci. Rep. 7, 43911 (2017). DOI:10.1038/srep43911
2. Shim, K., Gulhar, R., and Jialal, I. Exploratory metabolomics of nascent metabolic syndrome. J. Diabetes Complications 33(3), 212-216 (2019). DOI:10.1016/j.jdiacomp.2018.12.002
3. Palekar AG, et al. Accumulation of 50oxo-L-proline and 5-oxo-D-proline in the blood plasma in end stage renal disease. Biochem Med. 1975 Nov;14(3):339-45. DOI:10.1016/0006-2944(75)90052-6
4. D-Pyroglutamic Acid Production from L-Glutamic Acid by Successive Racemization, Resolution and Dehydration. DOI:10.6967/JCICE.200003.0177

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