γ-L-Glutamyl-L-alanine

• CAT Number: I011909
• CAS Number: 5875-41-2
• Molecular Formula: C8H14N2O5
• Molecular Weight: 218.21
• Purity: ≥95%
• Synonyms: (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
• InChIKey: WQXXXVRAFAKQJM-WHFBIAKZSA-N
• SMILES: CC(C(=O)O)NC(=O)CCC(C(=O)O)N

γ-L-Glutamyl-L-alanine, composed of gamma-glutamate and alanine, is a proteolytic breakdown product of larger proteins. γ-L-Glutamyl-L-alanine is a natural substrate of the γ-Glutamylcyclotransferase. γ-L-Glutamyl-L-alanine is a positive modulator of calcium-sensing receptor (CaR) function[1][2][3][4].
γ-L-Glutamyl-L-alanine (γ-Glu-Ala) shows the potency for Ca2+i mobilization in CaR (calcium-sensing receptor)-expressing HEK-293 cells, with an EC50 of 4.8 µM[3].
γ-L-Glutamyl-L-alanine shows the potency for Ca2+i mobilization in human parathyroid cells with an EC50 of 13.9 µM[3].
γ-L-Glutamyl-L-alanine (20 μM) suppress PTH secretion from normal human parathyroid cells[3].
γ-L-Glutamyl-L-alanine is a substrate for glutaminase B[4].

Reference

[1]. Ovchinnikova OG, et al. Structure of a polysaccharide from Providencia rustigianii O11 containing a novel amide of 2-acetamido-2-deoxygalacturonic acid with L-glutamyl-L-alanine. Carbohydr Res. 2012 Feb 15;349:95-102.
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[2]. York MJ, et al. gamma-Glutamylcyclotransferase: inhibition by D-beta-aminoglutaryl-L-alanine and analysis of the solvent kinetic isotope effect. Eur J Biochem. 1989 Sep 1;184(1):97-101.
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[3]. Broadhead GK, et al. Allosteric modulation of the calcium-sensing receptor by gamma-glutamyl peptides: inhibition of PTH secretion, suppression of intracellular cAMP levels, and a common mechanism of action with L-amino acids. J Biol Chem. 2011 Mar 18;286(11):8786-97.

[4]. Tatsuo Yamamoto, et al. Further Characterization of Glutaminase Isozymes from Pseudomonas aeruginosa.