γ-Glu-Phe (γ-Glutamylphenylalanine) is synthesized by Bacillus amyloliquefaciens (GBA) and Aspergillus oryzae (GAO). γ-Glu-Phe or the post-enzymatic reaction mixture enhances the umami intensity of commercial soy sauce and model chicken broth.
CAT No: HB00102
CAS No:7432-24-8
Synonyms/Alias:H-gamma-glu-phe-oh;7432-24-8;gamma-Glutamylphenylalanine;gamma-GLU-PHE;H-glu(phe-oh)-oh;glutamylphenylalanine;N-L-gamma-Glutamyl-3-phenyl-L-alanine;N-L-gamma-Glutamyl-L-phenylalanine;L-gamma-Glutamyl-L-phenylalanine;N-(gamma-L-Glutamyl)phenylalanine;(2S)-2-amino-5-[[(1S)-1-carboxy-2-phenylethyl]amino]-5-oxopentanoic acid;(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid;EINECS 231-077-0;MFCD00002629;L-gamma-Glu-L-Phe;H--Glu-Phe-OH;|A-Glutamylphenylalanine;gammaglutamylphenylalanine;SCHEMBL161658;(S)-2-Amino-5-(((S)-1-carboxy-2-phenylethyl)amino)-5-oxopentanoic acid;CHEBI:89582;DTXSID60995842;XHHOHZPNYFQJKL-QWRGUYRKSA-N;L-.gamma.-Glutamyl-L-phenylalanine;N-(.gamma.-L-Glutamyl)phenylalanine;CS-6416;FG36323;L-Phenylalanine, N-L-.gamma.-glutamyl-;DA-64142;MS-24209;HY-101399;NS00046055;G12037;Q27161779;N-(4-Amino-4-carboxy-1-hydroxybutylidene)phenylalanine;(S)-2-amino-5-((S)-1-carboxy-2-phenylethylamino)-5-oxopentanoic acid;
H-gamma-Glu-Phe-OH is a synthetic dipeptide composed of gamma-glutamyl and phenylalanine residues, structurally characterized by the presence of a gamma-peptide bond. As a member of the gamma-glutamyl peptide family, it serves as an important molecular tool for investigating peptide transport, metabolism, and enzymatic specificity. Its unique configuration, differing from typical alpha-peptides, makes it highly relevant for studies focused on gamma-glutamyl transferase activity, peptide stability, and the broader field of peptide biochemistry. Researchers value this compound for its ability to model non-canonical peptide linkages and to provide insight into the physiological and biochemical roles of gamma-glutamyl peptides in various biological systems.
Peptide Transport Studies: H-gamma-Glu-Phe-OH is widely employed in research exploring the mechanisms of peptide transport across cellular membranes. Its gamma-glutamyl linkage allows scientists to probe the substrate specificity and transport efficiency of peptide transporters, particularly those involved in the uptake and translocation of gamma-glutamyl peptides. By using this compound as a model substrate, researchers can delineate the structural requirements for transporter recognition and gain a deeper understanding of the molecular determinants that govern peptide movement in biological systems.
Enzymatic Activity Assays: The dipeptide is frequently utilized as a substrate in enzymological studies, especially those focusing on gamma-glutamyl transferase (GGT) and related enzymes. Its structure is particularly suitable for assessing enzyme kinetics, substrate specificity, and catalytic mechanisms. By monitoring the enzymatic cleavage or transfer of the gamma-glutamyl group, researchers can characterize the activity of GGT and other peptidases, facilitating the development of novel assay platforms and advancing knowledge of peptide metabolism.
Peptide Stability and Degradation Research: The presence of a gamma-glutamyl bond in H-gamma-Glu-Phe-OH offers a valuable system for investigating peptide stability and degradation pathways. Scientists use it to evaluate the susceptibility of gamma-linked peptides to enzymatic hydrolysis, compare the relative stability of gamma- versus alpha-peptide bonds, and elucidate the metabolic fate of non-standard peptides in biological matrices. These studies contribute to a broader understanding of peptide turnover and the factors influencing peptide half-life in physiological and experimental settings.
Peptide Synthesis Methodology: H-gamma-Glu-Phe-OH serves as a reference molecule in the development and optimization of synthetic protocols for gamma-glutamyl peptides. Its defined structure allows chemists to refine coupling strategies, optimize protecting group schemes, and troubleshoot synthetic challenges associated with gamma-linkages. By employing this dipeptide as a benchmark, researchers can improve the efficiency and fidelity of gamma-peptide synthesis, which is essential for expanding the repertoire of bioactive peptides available for research and industrial applications.
Analytical Method Development: The distinct physicochemical properties of this dipeptide make it a useful standard in the development and validation of analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry. Its use supports the calibration of detection methods for gamma-glutamyl peptides, enabling accurate quantification, purity assessment, and structural verification in complex mixtures. This facilitates high-quality analytical workflows in peptide research, quality control, and biochemical assay development.
2. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
3. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
4. TMEM16F and dynamins control expansive plasma membrane reservoirs
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