Pyroglutamyl-glutamyl-proline amide integrates a pyroglutamate cap with acidic and cyclic residues that influence backbone curvature. The peptide serves as a stable motif for hydrogen-bond and ring-conformation studies. Researchers analyze its behavior in enzymatic recognition and solvent interactions. Applications include structural modeling, peptide processing studies, and motif-function evaluation.
CAT No: R2506
CAS No:85541-78-2
Synonyms/Alias:85541-78-2;(Glu2)-TRH;pyroglutamyl-glutamyl-proline amide;Pglu-glu-pro-amide;pGlu-Glu-Pro-NH2;PYR-GLU-PRO-NH2;[Glu2]-TRH;NMJ3YG49SE;(4S)-5-[(2S)-2-carbamoylpyrrolidin-1-yl]-5-oxo-4-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoic acid;Pglu-glu-pronh2;Glp-glu-pronh2;Pyroglutamyl-glutamyl-prolineamide;PyroGLU-GLU-PRO AMIDE;Fertilization promoting peptide;Pyroglutamyl-glutamyl-prolinamide;(Glu2)-TRH Pyr-Glu-Pro-NH2;MFCD00076815;pGlu-Glu-Pro Amide;GLP-GLU-PRO-NH2;UNII-NMJ3YG49SE;pyroglutamylglutamylprolineamide;SCHEMBL1373186;CHEMBL3895280;CHEBI:183942;DTXSID501006105;HY-P3960;DA-69328;FG108676;CS-0634436;L-Prolinamide, 5-oxo-L-prolyl-L-alpha-glutamyl-;L-PROLINAMIDE, 5-OXO-L-PROLYL-L-.ALPHA.-GLUTAMYL-;(S)-5-((S)-2-carbamoylpyrrolidin-1-yl)-5-oxo-4-((S)-5-oxopyrrolidine-2-carboxamido)pentanoic acid;4-{[Hydroxy(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methylidene]amino}-5-{2-[hydroxy(imino)methyl]pyrrolidin-1-yl}-5-oxopentanoic acid;
Pyroglutamyl-glutamyl-proline amide is a synthetic tripeptide that features a pyroglutamyl residue at the N-terminus, followed by glutamyl and proline residues, and an amidated C-terminus. As a structurally defined peptide, it is of significant interest in biochemical research due to its sequence-specific properties, conformational stability, and potential to mimic naturally occurring peptide motifs. The presence of the pyroglutamyl group imparts resistance to exopeptidase degradation, while the proline residue can influence the peptide's secondary structure. Researchers utilize this compound to probe structure-activity relationships, investigate peptide stability, and explore molecular recognition events relevant to peptide-based signaling and regulation.
Peptide structure-function studies: Pyroglutamyl-glutamyl-proline amide serves as a valuable tool for elucidating the relationship between sequence composition and peptide conformation. The inclusion of a pyroglutamyl group at the N-terminus and an amidated C-terminus allows for the investigation of terminal modifications on peptide folding, stability, and resistance to enzymatic cleavage. Researchers employ this tripeptide to examine how such modifications affect biological half-life and binding affinity in model systems, providing insights that inform the rational design of more robust peptide analogs for biochemical assays.
Enzyme substrate specificity assays: The defined sequence of this tripeptide makes it suitable for use in studies of protease and peptidase substrate preferences. Its resistance to certain exopeptidases, due to the pyroglutamyl cap and C-terminal amidation, enables selective analysis of endopeptidase activity. By incorporating it into enzymatic assays, scientists can characterize the cleavage specificity of various proteolytic enzymes, map active sites, and screen for potential inhibitors, thereby advancing understanding of peptide metabolism and regulation.
Peptide synthesis research: Pyroglutamyl-glutamyl-proline amide is frequently utilized as a model system in the development and optimization of synthetic methodologies. Its sequence presents challenges such as proline-induced conformational constraints and terminal modifications, making it ideal for testing coupling strategies, protecting group compatibility, and purification protocols in solid-phase peptide synthesis. Outcomes from these studies contribute to improved synthetic efficiency and yield, benefiting the broader field of peptide chemistry.
Peptide-protein interaction analysis: The tripeptide is employed in experimental systems designed to dissect the molecular basis of peptide recognition by proteins, such as receptors or binding domains. Its unique sequence and modifications offer a platform for assessing the influence of terminal groups and proline residues on binding affinity, specificity, and conformational adaptability. Such studies are instrumental in mapping interaction motifs and guiding the development of peptide-based probes or modulators for research applications.
Analytical method development: Due to its well-defined structure, pyroglutamyl-glutamyl-proline amide is an effective standard or reference compound in the calibration and validation of analytical techniques, including high-performance liquid chromatography (HPLC) and mass spectrometry (MS). Its physicochemical properties, such as stability and predictable retention behavior, make it suitable for benchmarking peptide analysis workflows, ensuring accurate quantification, and facilitating method optimization in peptide research laboratories.
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