Met-Enkephalin

Met-enkephalin is a 5-amino acid endogenous peptide that acts as an agonist at opioid receptors. It is one of the first discovered endogenous opioid peptides, or opiopeptins, along with its congener, Leu-enkephalin.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Met-Enkephalin(CAS 58569-55-4)

CAT No: R1822

CAS No:58569-55-4

Synonyms/Alias:MET-enkephalin;58569-55-4;H-Tyr-Gly-Gly-Phe-Met-OH;Methionine enkephalin;Tyr-Gly-Gly-Phe-Met-OH;METENKEFALIN;TYR-GLY-GLY-PHE-MET;(Met5)-enkephalin;Metenkefalin [INN];[Met]enkephalin;[5-Methionine]Enkephalin;Opioid growth factor;ENKEPHALIN, METHIONINE;[Met5]-ENKEPHALIN;9JEZ9OD3AS;Porcine beta-endorphin 1-5;Sh-pentapeptide-19;CCRIS 4225;EINECS 261-335-8;(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid;1-5-Adrenorphin (human);Met-Enkephalin acetate salt;NSC 374896;opioid growth factor (OGF);Enkephalin-(5-l-methionine);CHEMBL13786;METENKEFALIN [WHO-DD];CHEBI:6618;DTXSID80332078;NSC-374896;MFCD00076415;[Met5]Enkephalin acetate salt hydrate;Metenkephalin;(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenyl-propanoyl]amino]-4-methylsulfanyl-butanoic acid;L-Methionine, L-tyrosylglycylglycyl-L-phenylalanyl-;Met Enkephalin;methionine-enkephalin;Adrenorphin (human), 6-de-L-arginine-7-de-L-arginine-8-de-L-valinamide-;(Met(5))enkephalin;[Met(5)]enkephalin;L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-L-METHIONINE .BETA.-ENDORPHIN HUMAN-(1-5)-PEPTIDE;(Met(5))-enkephalin;[Met(5)]-enkephalin;(2S,5S,14S)-14-Amino-5-benzyl-15-(4-hydroxyphenyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic acid;M-ENK;Met(5)-Enkephalin;5 Methionine Enkephalin;5-Methionine Enkephalin;82362-17-2;Enkephalin, 5-Methionine;UNII-9JEZ9OD3AS;L-Tyr-Gly-Gly-L-Phe-L-Met;met-enkefalin;H-L-Tyr-Gly-Gly-L-Phe-L-Met-OH;Met5-Enkephalin;NP2 Enkephalin;[Met]-enkephalin;Met-Enk;1-5 Adrenorphin;(2S)-2-(((2S)-2-((2-((2-(((2S)-2-amino-3-(4-hydroxyphenyl)propanoyl)amino)acetyl)amino)acetyl)amino)-3-phenyl-propanoyl)amino)-4-methylsulfanyl-butanoic acid;(2S)-2-(((2S)-2-((2-((2-(((2S)-2-amino-3-(4-hydroxyphenyl)propanoyl)amino)acetyl)amino)acetyl)amino)-3-phenylpropanoyl)amino)-4-methylsulfanylbutanoic acid;(2S)-2-(((2S)-2-((2-((2-(((2S)-2-azaniumyl-3-(4-hydroxyphenyl)propanoyl)amino)acetyl)amino)acetyl)amino)-3-phenylpropanoyl)amino)-4-methylsulfanylbutanoate;(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-azaniumyl-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoate;L-Tyrosylglycylglycyl-L-phenylalanyl-L-methionine;Inno-105;SCHEMBL632433;GTPL1614;DTXCID80283172;IRT-101;HY-P0073;SH-PENTAPEPTIDE-19 [INCI];BDBM50019056;AKOS030525639;CS-5426;DB12668;NCGC00163683-01;AS-58159;DA-75437;FM108776;H-Tyr-Gly-Gly-Phe-Met-OH; H-YGGFM-OH;NS00054117;C75740;Met-Enkephalin (H-L-Tyr-Gly-Gly-L-Phe-L-Met-OH);N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-methionine;L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-L-METHIONINE BETA-ENDORPHIN HUMAN-(1-5)-PEPTIDE;([Met]-enkephalin)2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid([Met]-enkephalin;(S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid;1632987-92-8;2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-1-oxo-3-phenyl-propylamino]-4-methylsulfanyl-butyric acid;2-[1-[1-amino-2-(4-hydroxyphenyl)-(1S)-ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenyl-(1S)-ethylcarboxamido]-4-methylsulfanyl-(2S)-butanoic acid;2-[2-(2-{2-[2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid;261-335-8;

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M.F/Formula
C27H35N5O7S
M.W/Mr.
573.7
Sequence
One Letter Code:YGGFM
Three Letter Code:H-Tyr-Gly-Gly-Phe-Met-OH
Appearance
White or off-white lyophilized powder
Purity
≥98%

Met-Enkephalin, also known as methionine-enkephalin, is a naturally occurring pentapeptide belonging to the endogenous opioid peptide family. Structurally, it is composed of a sequence of five amino acids and serves as a key neurotransmitter and neuromodulator in mammalian systems. Its primary function involves binding to opioid receptors, particularly the delta and, to a lesser extent, mu subtypes, where it modulates nociceptive signaling and various physiological processes. As a prototype member of the enkephalin class, Met-Enkephalin is widely utilized in research focused on neurobiology, pain modulation, and peptide-receptor interactions, offering valuable insights into the molecular mechanisms underlying opioid activity and peptide signaling pathways.

Neuroscience research: Met-Enkephalin is extensively applied in neurobiological studies to elucidate the roles of endogenous opioid peptides in central and peripheral nervous system function. Researchers employ this peptide to investigate synaptic transmission, neural plasticity, and the regulation of pain pathways. Its ability to selectively activate opioid receptors makes it an indispensable tool for dissecting the molecular underpinnings of analgesia, reward, and stress response, as well as for mapping the distribution and function of opioid systems in various brain regions.

Receptor binding assays: The pentapeptide is frequently used in binding studies to characterize the pharmacological properties and selectivity of opioid receptors. By serving as a reference ligand in radioligand displacement or fluorescence-based assays, it enables the quantification of receptor affinity, density, and subtype specificity. Such applications are critical for screening novel opioid receptor modulators, understanding receptor-ligand interactions at the molecular level, and advancing the development of receptor-targeted compounds for research purposes.

Peptide-receptor interaction studies: Met-Enkephalin plays a central role in structural and biophysical investigations aimed at deciphering the dynamics of peptide-receptor complexes. Through techniques such as NMR spectroscopy, X-ray crystallography, and computational modeling, scientists utilize this peptide to probe the conformational changes and binding interfaces involved in opioid receptor activation. These studies contribute to a deeper understanding of signal transduction mechanisms and inform rational design of peptide analogs with tailored receptor selectivity.

Peptide degradation and metabolism research: The stability and enzymatic breakdown of Met-Enkephalin are of significant interest in studies of peptide metabolism. Researchers use it as a model substrate to investigate the activity of peptidases such as enkephalinases and aminopeptidases, which regulate peptide half-life and bioavailability in biological systems. Insights gained from these experiments aid in elucidating the physiological control of endogenous opioid signaling and in developing strategies to modulate peptide stability for research applications.

Analytical method development: The compound is also utilized as a standard or analyte in the development and validation of analytical techniques for peptide detection and quantification. Methods such as high-performance liquid chromatography (HPLC), mass spectrometry, and immunoassays rely on Met-Enkephalin for calibration, sensitivity assessment, and specificity testing. These analytical applications support accurate measurement of peptide concentrations in complex biological matrices, facilitating studies in neurochemistry, pharmacokinetics, and peptide biomarker discovery.

Long-term Storage Conditions
DMSO : ≥ 40 mg/mL (69.73 mM)

H2O : 6.67 mg/mL (11.63 mM; Need ultrasonic)
InChI
InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
InChI Key
YFGBQHOOROIVKG-FKBYEOEOSA-N

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