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| | D-Pyroglutamic acid Basic information |
| | 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) |
| | 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 |
| | D-Pyroglutamic acid Preparation Products And Raw materials |
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