Met-Enkephalin-Arg-Phe extends the native enkephalin sequence with additional residues influencing binding and folding. The peptide supports research into receptor selectivity, aromatic stacking, and hydrophobic clustering. Researchers employ it to analyze extended opioid-like motifs. Its defined architecture aids structural investigations.
CAT No: PI-013
CAS No:73024-95-0
Synonyms/Alias:Met-enkephalin-Arg-Phe;73024-95-0;Tyr-gly-gly-phe-met-arg-phe;Yggfmrf;Met-enk-AP;Enkephalin met, heptapeptide;6-Arg-7-phe-met-enkephalin;Met-enkephalin, arg(6)-phe(7)-;enkephalin-Met, Arg(6)-Phe(7)-;Methionine-enkephalin, arg(6)-phe(7)-;(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoic acid;Enkephalin-met, arginyl(6)-phenylalanine(7)-;Methionine-enkephalin-arginine-phenylalanine;Tyrosyl-glycyl-glycyl-phenylalanyl-methionyl-arginyl-phenylalanine;L-Phenylalanine, N-(N(2)-(N-(N-(N-(N-L-tyrosylglycyl)glycyl)-L-phenylalanyl)-l-methionyl)-L-arginyl)-;MEAP peptide;MERF peptide;H-Tyr-Gly-Gly-Phe-Met-Arg-Phe-OH;MFCD00076425;CHEBI:80265;HY-P4196;DA-55364;FM108789;PD150438;CS-0647109;H-Tyr-Gly-Gly-Phe-Met-Arg-Phe-OH; H-YGGFMRF-OH;Met-Enkephalin-Arg-Phe (H-L-Tyr-Gly-Gly-L-Phe-L-Met-L-Arg-L-Phe-OH);(2S,5S,8S,11S,20S)-20-amino-2,11-dibenzyl-5-(3-guanidinopropyl)-21-(4-hydroxyphenyl)-8-(2-(methylthio)ethyl)-4,7,10,13,16,19-hexaoxo-3,6,9,12,15,18-hexaazahenicosan-1-oic acid;
Chemical Name:(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-phenylpropanoic acid
Met-Enkephalin-Arg-Phe is a synthetic peptide belonging to the extended enkephalin family, structurally characterized by the addition of arginine and phenylalanine residues to the native methionine-enkephalin pentapeptide. As a heptapeptide opioid, it serves as a valuable tool in neurochemical and receptor-binding studies due to its enhanced affinity and selectivity for certain opioid receptor subtypes. The compound's unique sequence enables researchers to probe peptide-receptor interactions, signal transduction pathways, and neuropeptide processing mechanisms with a high degree of specificity. Its biochemical relevance is underscored by its role in elucidating the structure-activity relationships within endogenous opioid systems, making it a critical resource for advancing neuropharmacological and peptide research.
Receptor Binding Studies: Met-Enkephalin-Arg-Phe is widely utilized in receptor-binding assays to investigate the pharmacological profiles of delta and mu opioid receptors. Its extended structure allows for the detailed mapping of ligand-receptor interactions, offering insights into receptor subtype selectivity and binding kinetics. Researchers employ this peptide to characterize the molecular determinants of opioid receptor affinity, which is essential for advancing the understanding of endogenous opioid signaling and for the design of novel ligands with tailored receptor specificity.
Neuropeptide Signaling Research: The compound is instrumental in studies focused on neuropeptide signaling pathways within the central nervous system. By serving as a model ligand, it facilitates the exploration of downstream effects following opioid receptor activation, including modulation of neurotransmitter release and neuronal excitability. These investigations contribute to a broader comprehension of how enkephalin analogs influence synaptic transmission and neural circuit function in both physiological and experimental settings.
Peptide Structure-Activity Relationship Analysis: Met-Enkephalin-Arg-Phe is frequently employed in structure-activity relationship (SAR) studies to dissect the influence of peptide sequence modifications on biological activity. The addition of arginine and phenylalanine residues provides a platform for systematic evaluation of side chain contributions to receptor binding and signal transduction efficacy. Such analyses are fundamental for guiding the rational design of peptide-based probes and functional analogs in neurochemical research.
Enzymatic Degradation and Metabolism Studies: The heptapeptide is utilized to assess the enzymatic stability and metabolic fate of opioid peptides in vitro. By monitoring the degradation pathways and identifying the specific peptidases involved, researchers gain valuable information about peptide half-life, bioavailability, and the impact of structural modifications on metabolic resistance. These studies inform the development of more stable peptide analogs for research applications where prolonged activity is desirable.
Peptide Synthesis and Analytical Method Development: Met-Enkephalin-Arg-Phe serves as a reference standard and test substrate in peptide synthesis optimization and analytical method development. Its well-defined sequence and physicochemical properties make it suitable for validating chromatographic separation techniques, mass spectrometric detection protocols, and peptide purification workflows. This utility supports the advancement of peptide chemistry methodologies and ensures the reliability of analytical results in both academic and industrial laboratory environments.
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