Endomorphin-1

Base Information

• Chemical Name: Endomorphin-1
• CAS No.: 189388-22-5
• Deprecated CAS: 1801442-15-8
• Molecular Formula: C₃₄H₃₈N₆O₅
• Molecular Weight: 610.713
• DSSTox Substance ID: DTXSID10415505
• Nikkaji Number: J830.103D
• Wikipedia: Endomorphin-1
• Wikidata: Q4531852
• Metabolomics Workbench ID: 38749
• ChEMBL ID: CHEMBL316446
• Mol file: 189388-22-5.mol

Synonyms:(Dmt1)endomorphin-1;endomorphin 1;endomorphin-1;Tyr-Pro-Trp-Phe-Nh2;tyrosyl-prolyl-tryptophyl-phenylalaninamide

Chemical Property of Endomorphin-1

Chemical Property:

• Appearance/Colour: Solid. (Solid powder.)
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 144-146℃
• Refractive Index: 1.671
• Boiling Point: 1052.765 °C at 760 mmHg
• PKA: 9.86±0.15(Predicted)
• Flash Point: 590.491 °C
• PSA: 183.64000
• Density: 1.343 g/cm³
• LogP: 3.79490
• Storage Temp.: −20°C
• Solubility.: ≥14.9 mg/mL in H2O; ≥30.55 mg/mL in DMSO; ≥47 mg/mL in EtOH
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 610.29036833
• Heavy Atom Count: 45
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

Endomorphin 1 ^*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=CNC4=CC=CC=C43)C(=O)NC(CC5=CC=CC=C5)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=CNC4=CC=CC=C43)C(=O)N[C@@H](CC5=CC=CC=C5)C(=O)N

Technology Process of Endomorphin-1

There total 25 articles about Endomorphin-1 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: 91.0%

Boc-Tyr-Pro-Trp-PheNH2 (351184-02-6) → endomorphin 1 (189388-22-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; Cooling with ice;

DOI:10.1039/c1gc15042a

Reference yield: 51.8%

Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → endomorphin 1 (189388-22-5)

Guidance literature:

Multistep reaction.;

DOI:10.1016/j.bmc.2008.04.020

Reference yield:

Boc-Tyr-OH (3978-80-1) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → endomorphin 1 (189388-22-5)

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; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Further stages;

DOI:10.1016/j.bmc.2020.115438

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Tyr-OH

Boc-Trp-OH

Refernces

• 1、 Cui, Jiaming,Han, Chao-zhen-yi,Liu, Xin,Luo, Keyao,Ma, Mengtao,Wang, Jing,Wang, Rui,Wang, Yuan,Wang, Zhaojuan,Yang, Dongxu,Zhang, Xianghui,Zhao, Long,Zhou, Jingjing. "Design, synthesis, and biological activity of new endomorphin analogs with multi-site modifications". . . Retrieved 2020/03/24.
• 2、 Sun, Honglin,He, Bingfang,Xu, Jiaxing,Wu, Bin,Ouyang, Pingkai. "Efficient chemo-enzymatic synthesis of endomorphin-1 using organic solvent stable proteases to green the synthesis of the peptide". . p. 1680 - 1685. Retrieved 2011/08/07.