A dipeptide
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γ-Glu-Ala (trifluoroacetate salt)

Item No. 36688

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-γ-glutamyl-L-alanine, trifluoroacetate salt
Synonyms
  • γ-Glutamylalanine
  • γ-L-Glutamyl-L-alanine
Molecular Formula
C8H14N2O5 • XCF3COOH
Formula Weight
218.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 5 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
OC([C@@H](N)CCC(N[C@@H](C)C(O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C8H14N2O5.C2HF3O2/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15;3-2(4,5)1(6)7/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15);(H,6,7)/t4-,5-;/m0./s1
InChi Key
CANGULKFMKIYBP-FHAQVOQBSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $62

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    100 mg

    $109

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    250 mg

    $244

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    500 mg

    $365

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    Product Description

    γ-Glu-Ala is an endogenous kokumi dipeptide composed of L-glutamic acid (Item No. 30377) and L-alanine (Item No. 29757) that has been found in P. roqueforti.1 It has also been found in several ripened cheeses, including Gouda, goat, and Milner cheeses. γ-Glu-Ala is a positive allosteric modulator of the calcium-sensing receptor (CaSR; EC50 = 4.8 µM in CaSR-expressing HEK293 cells).2 It induces glutathionuria in mice when administered at a dose of 4 mmol/kg.3 Plasma levels of γ-Glu-Ala are increased in malnourished neonatal mice.4 Increased serum levels of γ-Glu-Ala are positively associated with an increased risk of chronic kidney disease.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Toelstede, S., and Hofmann, T. Kokumi-active glutamyl peptides in cheeses and their biogeneration by Penicillium roquefortii. J. Agric. Food Chem. 57(9), 3738-3748 (2009).

    2. Broadhead, G.K., Mun, H.-C., Avlani, V.A., et al. Allosteric modulation of the calcium-sensing receptor by γ-glutamyl peptides: Inhibition of PTH secretion, suppression of intracellular cAMP levels, and a common mechanism of action with ʟ-amino acids. The Journal of Biological Chemisty 286(11), 8786-8797 (2011).

    3. Anderson, M.E., and Meister, A. Inhibition of γ-glutamyl transpeptidase and induction of glutathionuria by γ-glutamyl amino acids. Proc. Natl. Acad. Sci. USA 83(14), 5029-5032 (1986).

    4. Preidis, G.A., Keaton, M.A., Campeau, P.M., et al. The undernourished neonatal mouse metabolome reveals evidence of liver and biliary dysfunction, inflammation, and oxidative stress. J. Nutr. 144(3), 273-281 (2014).

    5. Kim, H., Yu, B., Li, X., et al. Serum metabolomic signatures of plant-based diets and incident chronic kidney disease. Am. J. Clin. Nutr. 116(1), 151-164 (2022).