Dermorphin

Base Information

• Chemical Name: Dermorphin
• CAS No.: 77614-16-5
• Molecular Formula: C40H50N8O10
• Molecular Weight: 802.885
• UNII: 2SEC01B703
• DSSTox Substance ID: DTXSID40228281
• Nikkaji Number: J21.370E
• Wikipedia: Dermorphin
• Wikidata: Q1771654
• ChEMBL ID: CHEMBL278789
• Mol file: 77614-16-5.mol

Synonyms:dermorphin;dermorphin, (2-L-Ala)-isomer;H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2;tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide

Chemical Property of Dermorphin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 157-159 °C
• Boiling Point: 1323.8°C at 760 mmHg
• PKA: 9.83±0.15(Predicted)
• Flash Point: 754.4°C
• PSA: 314.05000
• Density: 1.363g/cm³
• LogP: 3.98630
• Storage Temp.: ?20°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 19
• Exact Mass: 802.36498982
• Heavy Atom Count: 58
• Complexity: 1410

Purity/Quality:

99% ^*data from raw suppliers

Dermorphin trifluoroacetate salt ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)NC(CC1=CC=CC=C1)C(=O)NCC(=O)NC(CC2=CC=C(C=C2)O)C(=O)N3CCCC3C(=O)NC(CO)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)O)N
• Isomeric SMILES: C[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CO)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)O)N
• Uses: A mu-opioid receptor agonist

Technology Process of Dermorphin

There total 3 articles about Dermorphin 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: 80.0%

Z-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2 → dermorphin (77614-16-5)

Guidance literature:

With formic acid; palladium;

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2,35661-39-3,79990-15-1,136132-75-7) → dermorphin (77614-16-5)

Guidance literature:

Fmoc-Ser(tBu)-OH; With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; at 20 ℃; for 1h;

With piperidine; In 1-methyl-pyrrolidin-2-one; for 0.333333h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-alanine; Further stages;

DOI:10.1002/chem.201602432

Reference yield:

BOC-glycine (4530-20-5) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) + BOC-O-benzyl-L-serine (23680-31-1) → dermorphin (77614-16-5)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jm00364a016

upstream raw materials:

BOC-glycine

1-(tert-butoxycarbonyl)-L-proline

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

BOC-O-benzyl-L-serine

Downstream raw materials:

N-Acetyl-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH₂

Refernces

• 1、 Sivanandaiah, K. M.,Babu, V. V. Suresh,Renukeshwar, H. C.,Gangadhar, B. P.. "Iodotrichlorosilane as Nα-Z cleaving agent in solid phase synthesis of dermorphin and oxytocin". . p. 487 - 491. Retrieved 2007/10/02.