Methionine enkephalin

Base Information

• Chemical Name: Methionine enkephalin
• CAS No.: 58569-55-4
• Molecular Formula: C27H35 N5 O7 S
• Molecular Weight: 573.67
• European Community (EC) Number: 261-335-8
• UNII: 9JEZ9OD3AS
• DSSTox Substance ID: DTXSID80332078
• Nikkaji Number: J246.108K
• Wikipedia: Met-enkephalin
• Wikidata: Q1960495
• NCI Thesaurus Code: C91011
• Metabolomics Workbench ID: 69732
• ChEMBL ID: CHEMBL13786
• Mol file: 58569-55-4.mol

Synonyms:5 Methionine Enkephalin;5-Methionine Enkephalin;Enkephalin, 5-Methionine;Enkephalin, Methionine;Met Enkephalin;Met(5)-Enkephalin;Met-Enkephalin;Methionine Enkephalin

Chemical Property of Methionine enkephalin

Chemical Property:

• Appearance/Colour: White lyophilised solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 174-177 °C
• Refractive Index: 1.608
• Boiling Point: 1052.9 °C at 760 mmHg
• PKA: 3.23±0.10(Predicted)
• Flash Point: 590.6 °C
• PSA: 225.25000
• Density: 1.324 g/cm³
• LogP: 1.80830
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 16
• Exact Mass: 573.22571965
• Heavy Atom Count: 40
• Complexity: 847

Purity/Quality:

98% ^*data from raw suppliers

Enkephalin Met ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
• Isomeric SMILES: CSCC[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
• Recent ClinicalTrials: Clinical Trial to Evaluate the Efficacy and Safety of an Immunomodulatory Therapy for the Treatment of Patients With Moderate to Severe COVID-19 Infection
• Uses: Endogenous opioid peptide that also functions as a growth factor on many cell types at a receptor that is distinct from the neuronal opioid receptors

Technology Process of Methionine enkephalin

There total 91 articles about Methionine enkephalin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(S)-2-{(S)-2-[2-(2-{(S)-3-[4-(4-Bromo-phenoxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-acetylamino)-acetylamino]-3-phenyl-propionylamino}-4-methanesulfinyl-butyric acid → met-enkephalin (58569-55-4)

Guidance literature:

With p-cresol; dimethylsulfide; hydrogen fluoride; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)87499-7

Reference yield: 90.0%

boc-Tyr-Gly-Gly-Phe-Met-OH (59481-77-5) → met-enkephalin (58569-55-4)

Guidance literature:

With hydrogenchloride; acetic acid; for 1h;

DOI:10.1248/cpb.46.1672

Reference yield: 63.0%

C17H13NO10S2(2-)*2Na(1+) + C20H19NO10S3(2-)*2Na(1+) + C24H19NO10S2(2-)*2Na(1+) + C24H19NO11S2(2-)*2Na(1+) → met-enkephalin (58569-55-4)

Guidance literature:

C₂₀H₁₉NO₁₀S₃^(2-)*2Na⁽¹⁺⁾; With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime; In water; acetonitrile; at 20 ℃; for 0.75h;

With ethanolamine; In water; for 0.166667h;

C₁₇H₁₃NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; C₂₄H₁₉NO₁₀S₂^(2-)*2Na⁽¹⁺⁾; C₂₄H₁₉NO₁₁S₂^(2-)*2Na⁽¹⁺⁾; Further stages;

DOI:10.1002/anie.202003676

upstream raw materials:

boc-Tyr-Gly-Gly-Phe-Met-OH

methionine-enkephalin sulfoxide

C₄₁H₅₀N₆O₁₇S

Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met

Downstream raw materials:

methionine-enkephalin sulfoxide

C₂₇H₃₅N₅O₈S

YGGFMYGGFM

Refernces

• 1、 Tam, James P.,Heath, William F.,Merrifield, R. B.. "IMPROVED DEPROTECTION IN SOLID PHASE PEPTIDE SYNTHEIS: QUANTITATIVE REDUCTION OF METHIONINE SULFOXIDE TO METHIONINE DURING HF CLEAVAGE". . p. 2939 - 2942. Retrieved 1982.
• 2、 Khan, Riaz A.. "Synthesis of Met-enkephalin by solution-phase peptide synthesis methodology utilizing para-toluene sulfonic acid as N-terminal masking of l-methionine amino acid". . p. 884 - 888. Retrieved 2016/11/11.