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, also known as gamma-L-glutamyl-L-phenylalanine, is a dipeptide compound composed of gamma-linked glutamic acid and phenylalanine. Its unique gamma-peptide bond distinguishes it from more common alpha-peptide dipeptides, imparting distinct biochemical properties and resistance to certain enzymatic degradation. This characteristic makes H-gamma-Glu-Phe-OH a valuable tool in peptide chemistry research, enzymology, and the study of metabolic pathways involving glutamyl transferases. The compound's solubility and stability profile further support its use in a variety of experimental systems, enabling scientists to explore its interactions in both in vitro and in vivo models. Researchers are particularly interested in its role as a model substrate and its potential as a building block for the synthesis of more complex peptides or peptide-based conjugates.
Peptide substrate studies: H-gamma-Glu-Phe-OH serves as an important substrate for investigating the specificity and catalytic mechanisms of gamma-glutamyl transferases and related enzymes. By incorporating this dipeptide into enzymatic assays, researchers can elucidate the substrate preferences and kinetic parameters of transferases that act on gamma-glutamyl bonds. The use of this compound in such studies has contributed to a deeper understanding of enzymatic selectivity, which is essential for both basic biochemical research and the development of enzyme inhibitors or modulators targeting glutamyl pathways.
Peptide transport and metabolism: Gamma-L-glutamyl-L-phenylalanine is utilized in studies focused on peptide transport systems, particularly those involving the gamma-glutamyl cycle. Its distinctive structure allows scientists to track and characterize the uptake, transport, and metabolic fate of gamma-linked peptides in cellular models. These investigations provide valuable insights into the physiological roles of peptide transporters, as well as the regulation of amino acid homeostasis in various tissues.
Synthesis of peptide-based materials: The dipeptide's unique gamma-linkage makes it a versatile building block for the synthesis of novel peptide-based materials and conjugates. Researchers employ H-gamma-Glu-Phe-OH in solid-phase peptide synthesis and solution-phase coupling reactions to create gamma-glutamyl-containing peptides with tailored properties. Such materials are of interest for their potential applications in biomaterials research, drug delivery systems, and the design of functionalized peptides with enhanced stability or specific biological activities.
Biochemical assay development: Gamma-glutamyl dipeptides like H-gamma-Glu-Phe-OH are frequently incorporated into biochemical assays designed to monitor enzyme activity, screen for modulators, or validate assay performance. The compound's stability and well-defined structure make it an ideal candidate for use as a reference substrate or control in high-throughput screening platforms. These applications facilitate the identification of new enzyme inhibitors or activators and support the optimization of assay conditions for reliable and reproducible results.
Analytical method validation: In analytical chemistry, H-gamma-Glu-Phe-OH is employed as a standard or reference compound for the validation of chromatographic and spectroscopic techniques. Its defined molecular structure and physicochemical properties enable accurate calibration and quantification in peptide analysis workflows. Researchers leverage this dipeptide to ensure the precision, accuracy, and sensitivity of analytical methods used in peptide characterization, quality control, and biomarker discovery. The use of gamma-glutamyl dipeptides in method validation ultimately contributes to the advancement of peptide research and the development of robust analytical platforms for a variety of scientific applications.
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