γ-Glu-Ala is a dipeptide composed of gamma-glutamate and alanine and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives, which formed an amide bond with the nitrogen of L-alanine at the γ carboxylic acid moiety of glutamate. γ-Glu-Ala is the natural substrate of CRF21 (γ-Glutamylcyclotransferase, GGCT).
CAT No: 10-101-278
CAS No:5875-41-2
Synonyms/Alias:5875-41-2;H-GAMMA-GLU-ALA-OH;gamma-Glu-Ala;gamma-L-Glutamyl-L-alanine;gamma-Glutamylalanine;5-L-Glutamyl-L-alanine;g-Glu-Ala;H-Glu(Ala-OH)-OH;L-gamma-glutamyl-L-alanine;(2S)-2-Amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid;(S)-2-Amino-5-(((S)-1-carboxyethyl)amino)-5-oxopentanoic acid;gamma-Gln-ala;(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid;g-Glutamylalanine;5-L-glutamylalanine;MFCD00037215;L-gamma-Glu-L-Ala;gamma-Glutamyl-alanine;H--Glu-Ala-OH;g-L-Glutamyl-L-alanine;H-GLU(ALA)-OH;N-L-gamma-glutamyl-L-alanine;SCHEMBL3707747;CHEBI:50619;DTXSID80974270;L-Alanine, N-L-gamma-glutamyl-;gamma-L-Glutamyl-L-alanine, 98%;AS-83087;DA-74123;HY-112171;CS-0043596;5-[(1-Carboxyethyl)imino]-5-hydroxynorvaline;E85624;Q27122149;
γ-Glu-Ala, also known as gamma-glutamyl-alanine, is a dipeptide composed of glutamic acid and alanine linked via a gamma-peptide bond. As a naturally occurring and synthetically accessible peptide, it serves as a valuable model compound in studies of peptide metabolism, enzymatic specificity, and peptide transport mechanisms. Its unique gamma-linkage distinguishes it from standard alpha-peptides, making it particularly relevant for research focused on the gamma-glutamyl cycle, peptide stability, and the biochemical pathways involving glutathione metabolism. The compound's structural features and functional groups enable its use in a variety of biochemical and analytical investigations, supporting both fundamental research and applied studies in peptide science.
Peptide metabolism research: γ-Glu-Ala is frequently utilized as a substrate to investigate the activity and specificity of gamma-glutamyl transferases and related enzymes. By serving as a model dipeptide, it facilitates the study of enzymatic cleavage and transfer reactions within the gamma-glutamyl cycle, which is central to amino acid transport and glutathione homeostasis in cells. Researchers use it to elucidate the mechanisms of peptide bond hydrolysis and to characterize enzyme kinetics, providing insights into metabolic regulation and the physiological roles of gamma-glutamyl peptides.
Transport mechanism studies: The compound is instrumental in probing the function of peptide transporters, particularly those involved in the uptake and translocation of gamma-glutamyl peptides across cellular membranes. Its defined structure and stability make it suitable for use in transport assays, tracer studies, and uptake experiments in cultured cells or membrane vesicle systems. These applications contribute to a deeper understanding of nutrient absorption, peptide carrier specificity, and the molecular determinants governing peptide trafficking in biological systems.
Peptide synthesis and analytical standards: γ-Glu-Ala serves as a reference standard and calibration compound in peptide synthesis protocols and analytical method development. Its well-characterized structure makes it ideal for validating chromatographic separation techniques, mass spectrometric detection, and quantitative peptide assays. Synthetic chemists and analytical laboratories employ it to optimize peptide purification strategies, assess method reproducibility, and ensure the accuracy of peptide quantification in complex mixtures.
Glutathione pathway investigations: The dipeptide is relevant in studies exploring the metabolism and turnover of glutathione, a critical cellular antioxidant. As an intermediate or product in gamma-glutamyl cycle reactions, it can be used to monitor enzymatic processes that regulate glutathione synthesis, degradation, and recycling. These experiments provide valuable data on oxidative stress responses, redox regulation, and cellular detoxification mechanisms, supporting research in cell biology, toxicology, and metabolic biochemistry.
Biochemical assay development: γ-Glu-Ala is employed in the development and validation of biochemical assays targeting gamma-glutamyl enzyme activities. Its defined chemical properties and reactivity enable precise measurement of enzyme function in biological samples, facilitating the screening of enzyme inhibitors, the assessment of metabolic disorders, and the discovery of novel modulators of peptide metabolism. The compound's versatility in assay design supports a wide range of research applications, from fundamental enzymology to applied biochemical analysis.
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