ENDOMORPHIN-2

Base Information

• Chemical Name: ENDOMORPHIN-2
• CAS No.: 141801-26-5
• Molecular Formula: C32H37 N5 O5
• Molecular Weight: 571.676
• UNII: 3PH5M0466G
• DSSTox Substance ID: DTXSID70415506
• Nikkaji Number: J454.979A
• Wikipedia: Endomorphin-2
• Wikidata: Q19597070
• Metabolomics Workbench ID: 38750
• ChEMBL ID: CHEMBL333357
• Mol file: 141801-26-5.mol

Synonyms:12:PN: WO2008052043 SEQID: 11 claimed protein; 2: PN: EP1782819 PAGE: 14 claimedprotein; 40: PN: WO2005016244 PAGE: 68 claimed protein; Endomorphin 2

Chemical Property of ENDOMORPHIN-2

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 130-131℃
• Boiling Point: 972.4°Cat760mmHg
• PKA: 9.86±0.15(Predicted)
• Flash Point: 541.9°C
• PSA: 167.85000
• Density: 1.292g/cm³
• LogP: 3.31360
• Storage Temp.: −20°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 571.27946930
• Heavy Atom Count: 42
• Complexity: 911

Purity/Quality:

99%, ^*data from raw suppliers

Endomorphin-2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)C(CC2=CC=C(C=C2)O)N)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CC4=CC=CC=C4)C(=O)N
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CC2=CC=C(C=C2)O)N)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N
• Uses: Endomorphin-2 is a potent and selective endogenous agonist for the μ-opiate receptor.

Technology Process of ENDOMORPHIN-2

There total 10 articles about ENDOMORPHIN-2 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: 45.0%

Boc-Tyr-Pro-Phe-Phe-NH2 (141801-21-0) → endomorphin II (141801-26-5)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1246/bcsj.65.1052

Reference yield:

Boc-Tyr-OH (3978-80-1) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) → endomorphin II (141801-26-5)

Guidance literature:

N-Fmoc L-Phe; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 1h; Inert atmosphere;

With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 0.25h; Inert atmosphere;

Boc-Tyr-OH; Fmoc-Pro-OH; N-Fmoc L-Phe; Further stages;

DOI:10.1016/j.bmc.2020.115438

Reference yield:

Z-Tyr-Pro-Phe-Phe-NH2 (907198-94-1) → endomorphin II (141801-26-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 5h;

DOI:10.1016/j.bmc.2008.05.001

upstream raw materials:

Boc-Tyr-Pro-Phe-Phe-NH₂

1-(tert-butoxycarbonyl)-L-proline

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Tyr-OH

Refernces

Cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues: Part 2

10.1021/jm300947s

The study focuses on the synthesis and evaluation of cyclic and linear analogues of endomorphin-2 (EM-2), a potent opioid peptide. The researchers replaced the native Pro2 residue with cis-4-amino-L-proline (cAmp) to create a more constrained cyclic structure and introduced variations in the stereochemistry of the Phe3 and Phe4 residues to modulate receptor affinity. They synthesized eight new analogues with different stereochemical configurations at the chiral centers of these aromatic residues. The aim was to enhance the affinity and activity towards μ-opioid receptors. The study found that the stereochemical changes led to significant improvements in affinity and activity compared to the prototype compound, with some analogues showing nanomolar binding affinity. The results provide insights into the structural requirements for optimal receptor interaction and could inform the development of more effective opioid therapeutics.

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