60283-51-4

Basic information

• Product Name: (MET(O)5)-ENKEPHALIN
• Synonyms: TYR-GLY-GLY-PHE-MET(O);(MET(O)5)-ENKEPHALIN;H-TYR-GLY-GLY-PHE-MET(O)-OH;enkephalin-Met, sulfoxide-
• CAS NO: 60283-51-4
• Molecular Formula: C₂₇H₃₅N₅O₈S
• Molecular Weight: 589.66
• Mol File: 60283-51-4.mol

Chemical Properties

• Boiling Point: 1131.6°C at 760 mmHg
• Flash Point: 638.2°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: -15°C
• PKA: 3.15±0.10(Predicted)
• CAS DataBase Reference: (MET(O)5)-ENKEPHALIN(CAS DataBase Reference)
• NIST Chemistry Reference: (MET(O)5)-ENKEPHALIN(60283-51-4)
• EPA Substance Registry System: (MET(O)5)-ENKEPHALIN(60283-51-4)

Safety Data

• Hazardous Substances Data: 60283-51-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(MET(O)5)-ENKEPHALIN is used as an analgesic agent for its ability to alleviate pain and reduce the sensation of pain in the body. It is particularly effective in managing chronic and acute pain conditions by binding to opioid receptors in the brain, spinal cord, and other parts of the body, leading to the reduction of pain signals and the release of feel-good hormones.
Used in Neurological Research:
(MET(O)5)-ENKEPHALIN is used as a research tool for studying the mechanisms of pain perception and the role of endorphins in the central nervous system. Its potential therapeutic benefits are being explored for the treatment of various neurological conditions, including pain disorders, addiction, and mood disorders.
Used in Drug Development:
(MET(O)5)-ENKEPHALIN serves as a lead compound in the development of novel pain management therapies. Its unique mechanism of action and potential for targeted delivery make it an attractive candidate for the creation of new drugs with improved efficacy and reduced side effects compared to existing opioid-based treatments.

InChI:InChI=1/C27H35N5O8S/c1-41(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-,41?/m0/s1

Upstream product

• 58569-55-4 met-enkephalin 

Downstream Products

• 58569-55-4 met-enkephalin 

Relevant articles and documents

Pharmaceutical Excipients Enhance Iron-Dependent Photo-Degradation in Pharmaceutical Buffers by near UV and Visible Light: Tyrosine Modification by Reactions of the Antioxidant Methionine in Citrate Buffer

Purpose: To evaluate the effect of excipients, including sugars and amino acids, on photo-degradation reactions in pharmaceutical buffers induced by near UV and visible light. Methods: Solutions of citrate or acetate buffers, containing 1 or 50?μM Fe3+, the model peptides methionine enkephalin (MEn), leucine enkephalin (LEn) or proctolin peptide (ProP), in the presence of commonly used amino acids or sugars, were photo-irradiated with near UV or visible light. The oxidation products were analyzed by reverse-phase HPLC and HPLC-MS/MS. Results: The sugars mannitol, sucrose and trehalose, and the amino acids Arg, Lys, and His significantly promote the oxidation of peptide Met to peptide Met sulfoxide. These excipients do not increase the yields of hydrogen peroxide, suggesting that other oxidants such as peroxyl radicals are responsible for the oxidation of peptide Met. The addition of free Met reduces the oxidation of peptide Met, but, in citrate buffer, causes the addition of Met oxidation products to Tyr residues of the target peptides. Conclusions: Commonly used excipients enhance the light-induced oxidation of amino acids in model peptides.

Repurposing the Pummerer Rearrangement: Determination of Methionine Sulfoxides in Peptides

The reversible oxidation of methionine residues in proteins has emerged as a biologically important post-translational modification. However, detection and quantitation of methionine sulfoxide in proteins is difficult. Our aim is to develop a method for specifically derivatizing methionine sulfoxide residues. We report a Pummerer rearrangement of methionine sulfoxide treated sequentially with trimethylsilyl chloride and then 2-mercaptoimidazole or pyridine-2-thiol to produce a dithioacetal product. This derivative is stable to standard mass spectrometry conditions, and its formation identified oxidized methionine residues. The scope and requirements of dithioacetal formation are reported for methionine sulfoxide and model substrates. The reaction intermediates have been investigated by computational techniques and by 13C NMR spectroscopy. These provide evidence for an α-chlorinated intermediate. The derivatization allows for detection and quantitation of methionine sulfoxide in proteins by mass spectrometry and potentially by immunochemical methods.

Reduction of methionine sulfoxide with NH4I/TFA: Compatibility with peptides containing cysteine and aromatic amino acids

The reduction of methionine sulfoxide with ammonium iodide in trifluoroacetic acid has been studied in peptides containing cysteine, histidine, tyrosine or tryptophan residues. While histidine and tyrosine have proved to be stable under the experimental conditions, cysteine is oxidized to cystine and tryptophan dimerizes to form 2-indolylindolenine derivatives. The use of methyl sulfide to increase the reduction rate minimizes the problem and protection of indole ring with the formyl group avoids the side reaction for this amino acid.