L-γ-Glutamyl-L-Isoleucine links a γ-glutamyl moiety to hydrophobic isoleucine, creating a dipeptide useful for studying γ-linkage chemistry. Researchers examine its conformational preferences and enzymatic susceptibility. The sequence models γ-glutamyl transfer processes. Applications include food chemistry, peptide-transport studies, and metabolic mechanistic research.
CAT No: R2599
CAS No:23632-83-9
Synonyms/Alias:gamma-Glu-Ile;L-gamma-Glu-L-Ile;L-gamma-glutamyl-L-isoleucine;gamma-glutamylisoleucine;23632-83-9;CHEBI:68434;DTXSID201311909;g-Glu-Ile;(2S,3S)-2-[(4S)-4-amino-4-carboxybutanamido]-3-methylpentanoic acid;(2S,3S)-2-(((4S)-4-amino-4-carboxybutanoyl)amino)-3-methylpentanoic acid;(2S,3S)-2-((4S)-4-amino-4-carboxybutanamido)-3-methylpentanoic acid;(2S,3S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-methylpentanoic acid;SCHEMBL236278;L-I(3)-Glutamyl-L-isoleucine;DTXCID201741722;EN300-28246534;Q27136933;870-192-6;
L-gamma-glutamyl-L-isoleucine is a dipeptide compound composed of the amino acids gamma-glutamic acid and isoleucine, joined via a gamma-peptide bond. As a member of the gamma-glutamyl dipeptide class, it exhibits unique biochemical properties that distinguish it from conventional alpha-peptides, particularly in terms of stability and resistance to proteolytic degradation. Its presence in biological systems has been associated with specific metabolic pathways, and it is of considerable interest in the study of peptide transport, enzymatic specificity, and amino acid metabolism. The compound's structural features make it a valuable tool for researchers investigating peptide function, enzymology, and the physiological roles of modified peptides.
Peptide transport studies: L-gamma-glutamyl-L-isoleucine is frequently utilized in research focused on peptide transport mechanisms, especially those involving gamma-glutamyl transpeptidase and related enzymes. The gamma-glutamyl linkage serves as a model substrate for probing the specificity and kinetics of transporters responsible for the uptake and processing of gamma-linked peptides. By tracking the uptake and metabolism of this dipeptide in cellular or vesicular systems, researchers can elucidate the roles of gamma-glutamyl peptides in nutrient absorption and cellular signaling.
Enzyme substrate specificity: In enzymology, this dipeptide is employed to investigate the substrate preferences and catalytic mechanisms of gamma-glutamyl transpeptidase and other peptidases that recognize gamma-glutamyl bonds. Its defined structure allows for controlled in vitro assays that differentiate between enzymes capable of cleaving gamma versus alpha peptide linkages. Such studies are critical for characterizing enzyme function, understanding substrate-enzyme interactions, and developing selective inhibitors or probes for gamma-glutamyl processing enzymes.
Metabolic pathway elucidation: The compound serves as a valuable probe in the study of amino acid and peptide metabolism, particularly within the gamma-glutamyl cycle. By incorporating L-gamma-glutamyl-L-isoleucine into metabolic assays, scientists can monitor its conversion, breakdown, or transport, thereby gaining insights into the regulation and flux of gamma-glutamyl compounds in various tissues. This approach aids in mapping the biochemical pathways involved in glutathione metabolism, detoxification processes, and cellular redox balance.
Analytical method development: L-gamma-glutamyl-L-isoleucine is also used as a reference standard or calibration compound in chromatographic and mass spectrometric methods designed to detect and quantify gamma-glutamyl peptides. Its well-defined structure and physicochemical properties make it suitable for optimizing analytical protocols, validating detection limits, and establishing retention times in complex biological samples. Such applications support both basic research and quality control in peptide analysis.
Peptide synthesis and structural studies: In the context of synthetic chemistry and structural biology, this dipeptide is employed as a building block or model system for the synthesis of gamma-glutamyl-containing peptides. Its incorporation into longer peptide chains enables researchers to explore the effects of gamma-linkages on peptide conformation, stability, and function. Furthermore, detailed spectroscopic and crystallographic studies using this compound contribute to a deeper understanding of the structural determinants governing peptide behavior and interactions in biological systems.
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