L-Pyroglutamic acid 7-amido-4-methylcoumarin
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L-Pyroglutamic acid 7-amido-4-methylcoumarin

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Sensitive fluorogenic substrate for pyrrolidonylpeptidase.

Category
Other Unnatural Amino Acids
Catalog number
BAT-008010
CAS number
66642-36-2
Molecular Formula
C15H14N2O4
Molecular Weight
286.28
L-Pyroglutamic acid 7-amido-4-methylcoumarin
IUPAC Name
(2S)-N-(4-methyl-2-oxochromen-7-yl)-5-oxopyrrolidine-2-carboxamide
Synonyms
L-Pyroglutamic acid-AMC
Appearance
White to off-white crystalline powder
Purity
≥ 98% (HPLC)
Density
1.393 g/cm3
Boiling Point
653.4ºC at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H14N2O4/c1-8-6-14(19)21-12-7-9(2-3-10(8)12)16-15(20)11-4-5-13(18)17-11/h2-3,6-7,11H,4-5H2,1H3,(H,16,20)(H,17,18)/t11-/m0/s1
InChI Key
GMVNXBGNKSQHIT-NSHDSACASA-N
Canonical SMILES
CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C3CCC(=O)N3
1. Side reactions in the pyroglutamic acid-7-amino-4-methylcoumarin synthesis
U Kalejs, J Karlson, Z Tetere, G Kreishman, M Petrova, E Brooks, D Zicane Int J Pept Protein Res . 1996 Jul;48(1):56-8. doi: 10.1111/j.1399-3011.1996.tb01106.x.
N-Formylpyroglutamic acid-7-amido-4-methylcoumarine and pyroglutamyl-pyroglutamic acid-7-amido-4-methylcoumarin are the major products in the synthesis of pyroglutamic acid-7-amido-4-methylcoumarin by phosphorus pentachloride in dimethylformamide and dicyclohexylcarbodiimide under pyridine activation.
2. Pyroglutamyl peptidase II inhibition enhances the analeptic effect of thyrotropin-releasing hormone in the rat medial septum
Ivan Lazcano, Miguel Angel Vargas, Rosa Maria Uribe, Magdalini Matziari, Erick Martínez-Chávez, Jean-Louis Charli, Patricia Joseph-Bravo J Pharmacol Exp Ther . 2012 Jul;342(1):222-31. doi: 10.1124/jpet.112.192278.
Thyrotropin-releasing hormone (TRH; pGlu-His-Pro-NH(2)) has multiple, but transient, homeostatic functions in the brain. It is hydrolyzed in vitro by pyroglutamyl peptidase II (PPII), a narrow specificity ectoenzyme with a preferential localization in the brain, but evidence that PPII controls TRH communication in the brain in vivo is scarce. We therefore studied in male Wistar rats the distribution of PPII mRNA in the septum and the consequence of PPII inhibition on the analeptic effect of TRH injected into the medial septum. Twelve to 14% of cell profiles expressed PPII mRNA in the medial septum-diagonal band of Broca; in this region the specific activity of PPII was relatively high. Twenty to 35% of PPII mRNA-labeled profiles were positive for TRH-receptor 1 (TRH-R1) mRNA. The intramedial septum injection of TRH reduced, in a dose-dependent manner, the duration of ethanol-induced loss of righting reflex (LORR). Injection of the PPII inhibitor pGlu-Asn-Pro-7-amido-4-methylcoumarin into the medial septum enhanced the effect of TRH. The injection of a phosphinic TRH analog, a higher-affinity inhibitor of PPII, diminished the duration of LORR by itself. In contrast, the intraseptal injection of pGlu-Asp-Pro-NH(2), a peptide that did not inhibit PPII activity, or an inhibitor of prolyl oligopeptidase did not change the duration of LORR. We conclude that in the medial septum PPII activity may limit TRH action, presumably by reducing the concentration of TRH in the extracellular fluid around cells coexpressing PPII and TRH-R1.
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