5-Oxo-D-prolin

Bezeichnung:5-Oxo-D-prolin

CAS-Nr4042-36-8

Englisch Name:D-Pyroglutamic acid

CBNumberCB0271107

SummenformelC5H7NO3

Molgewicht129.11

MOL-Datei4042-36-8.mol

Synonyma

5-Oxo-D-prolin

5-Oxo-D-prolin physikalisch-chemischer Eigenschaften

Schmelzpunkt	155-162 °C
alpha	27.5 º (c=10,1N NaOH)
Siedepunkt	239.15°C (rough estimate)
Dichte	1.3816 (rough estimate)
Brechungsindex	10 ° (C=5, H2O)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Dimethylformamide, DMSO (Slightly), Methanol (Slightly), Water
Aggregatzustand	Solid
pka	3.48±0.20(Predicted)
Farbe	Off-White to Light Beige
Optische Aktivität	[α]22/D +10°, c = 1.5 in H2O
Wasserlöslichkeit	soluble
Merck	14,8001
BRN	82133
InChIKey	ODHCTXKNWHHXJC-GSVOUGTGSA-N
CAS Datenbank	4042-36-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
HS Code	29339900

Gefahreninformationscode (GHS)

D-Pyroglutamic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
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.
Biologische Aktivität
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.
läuterung methode
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.]
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

5-Oxo-D-prolin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

4042-36-8, D-Pyroglutamic acid Verwandte Suche:

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