γ-Glu-Glu

γ-Glu-Glu is a dipeptide, made of two amino acids: gamma-glutamate (γ-Glu) and glutamate (Glu).

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
γ-Glu-Glu(CAS 1116-22-9)

CAT No: 10-101-297

CAS No:1116-22-9

Synonyms/Alias:1116-22-9;H-Gamma-Glu-Glu-OH;gamma-Glutamylglutamate;gamma-GLU-GLU;gamma-L-glutamyl-L-glutamic acid;G-Glu-Glu;H-Glu(Glu-OH)-OH;(S)-2-((S)-4-Amino-4-carboxybutanamido)pentanedioic acid;gamma-glutamylglutamic acid;N-gamma-L-Glutamyl-L-glutamic acid;(5-L-Glutamyl)-L-glutamate;L-|A-Glutamyl-L-glutamic acid;(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid;6018KCN7X2;gamma-l-glutamyl-l-glutamate;MFCD00002630;(2~{S})-2-[[(4~{S})-4-azanyl-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]pentanedioic acid;LysW-glutamate;LysW-L-glutamate;EINECS 214-233-2;gamma-L-Glu-L-Glu;Gamma Glutamylglutamic acid;5-GLUTAMYL GLUTAMATE;L--Glutamyl-L-glutamic acid;SCHEMBL236257;UNII-6018KCN7X2;CHEBI:73705;DTXSID20912237;gamma-L-Glutamyl L-Glutamic Acid;.gamma.-L-glutamyl-L-glutamic acid;.GAMMA.-GLUTAMYLGLUTAMIC ACID;LysW-gamma-(L-glutamyl)-L-glutamate;AKOS016014286;AS-76975;DA-74124;FG108030;L-Glutamic acid, N-L-.gamma.-glutamyl-;HY-118090;L-.GAMMA.-GLUTAMYL-L-GLUTAMIC ACID;CS-0065178;L-GLUTAMIC ACID, L-.GAMMA.-GLUTAMYL-;C05282;C20948;G77234;N-(4-Amino-4-carboxybutanoyl)glutamic acid #;GLUTAMIC ACID, N-L-.GAMMA.-GLUTAMYL-, L-;Q27143983;N-(4-Amino-4-carboxy-1-hydroxybutylidene)glutamic acid;(2S)-2-[(4S)-4-amino-4-carboxybutanamido]pentanedioic acid;KSN;

Chemical Name:(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid

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M.F/Formula
C10H16N2O7
M.W/Mr.
276.24
Sequence
One Letter Code:XE
Three Letter Code:H-gGlu-Glu-OH
Purity
≥97% by HPLC

γ-Glu-Glu, also known as gamma-glutamylglutamic acid, is a dipeptide composed of two glutamic acid residues linked via a gamma-glutamyl bond. This unique structure imparts distinctive physicochemical properties, making it a valuable research tool in various biochemical and physiological studies. As a naturally occurring compound, γ-Glu-Glu is often investigated for its role in metabolic pathways, particularly those related to amino acid transport and glutathione metabolism. Its stability and solubility in aqueous environments further enhance its utility in experimental protocols, enabling researchers to explore its function in diverse biological contexts. The compound's relevance in cellular and molecular research continues to expand, driven by its involvement in fundamental biological processes and potential as a model substrate.

Biochemical Pathway Elucidation: γ-Glu-Glu serves as an important probe for studying the gamma-glutamyl cycle, a metabolic pathway critical for amino acid transport and glutathione turnover. By incorporating this dipeptide into in vitro or in vivo experiments, researchers can trace the enzymatic activities of gamma-glutamyl transpeptidase and related enzymes. This approach provides insights into the mechanisms of amino acid uptake, detoxification, and cellular redox balance, shedding light on the regulation of glutathione homeostasis and the broader implications for oxidative stress response.

Enzyme Substrate Research: As a synthetic analog of naturally occurring gamma-glutamyl peptides, γ-Glu-Glu is frequently utilized as a model substrate in enzymology studies. It enables the characterization of substrate specificity, catalytic efficiency, and inhibition profiles of enzymes such as gamma-glutamyl transferase and peptidases. By monitoring the hydrolysis or transfer reactions involving this dipeptide, scientists can assess enzyme kinetics and identify potential modulators, advancing the understanding of enzyme function in health and disease.

Nutritional and Food Science Studies: The application of gamma-glutamylglutamic acid extends to nutritional research, where it is investigated for its role in flavor development and nutrient absorption. In food science, this dipeptide is studied for its contribution to the umami taste profile and its interaction with other amino acids or peptides in complex food matrices. Its presence and transformation during food processing or fermentation are of particular interest, as these factors influence both sensory properties and nutritional value.

Cellular Transport Mechanism Analysis: Researchers employ γ-Glu-Glu to probe the activity of amino acid transporters and peptide uptake systems in cellular models. By tracking the uptake and intracellular fate of the dipeptide, it is possible to delineate the specificity and regulation of transporter proteins involved in nutrient assimilation and metabolic signaling. This application is especially relevant for studying tissue-specific transport phenomena and the adaptation of cells to varying nutritional environments.

Biomarker Discovery and Analytical Method Development: The use of gamma-glutamylglutamic acid in metabolomics and analytical chemistry facilitates the identification of novel biomarkers and the refinement of detection techniques. As a representative compound in targeted or untargeted analyses, it aids in the quantification of gamma-glutamyl peptides in biological samples. This supports the development of sensitive assays for monitoring metabolic flux, disease progression, or response to interventions, thereby expanding the toolkit available for biochemical research and diagnostics.

Peptide Synthesis and Structure-Activity Relationship Studies: γ-Glu-Glu plays a significant role in peptide synthesis and the investigation of structure-activity relationships within peptide families. By serving as a building block or reference compound, it allows chemists to design and evaluate new peptides with tailored properties for research or industrial applications. Its well-characterized structure makes it an ideal candidate for comparative studies, helping to elucidate how subtle modifications in peptide sequence or conformation influence biological activity, stability, and interaction with target molecules.

Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
Evaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
InChI
InChI=1S/C10H16N2O7/c11-5(9(16)17)1-3-7(13)12-6(10(18)19)2-4-8(14)15/h5-6H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)(H,18,19)/t5-,6-/m0/s1
InChI Key
OWQDWQKWSLFFFR-WDSKDSINSA-N
Canonical SMILES
C(CC(=O)NC(CCC(=O)O)C(=O)O)C(C(=O)O)N
Isomeric SMILES
C(CC(=O)N[C@@H](CCC(=O)O)C(=O)O)[C@@H](C(=O)O)N

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