L-Tyrosyl-D-methionylglycyl-L-phenylalanyl-L-prolinamide

Base Information

• Chemical Name: L-Tyrosyl-D-methionylglycyl-L-phenylalanyl-L-prolinamide
• CAS No.: 63307-63-1
• Molecular Formula: C30H40 N6 O6 S
• Molecular Weight: 612.7402
• DSSTox Substance ID: DTXSID80979407
• Nikkaji Number: J265.189K
• Wikidata: Q76010406
• ChEMBL ID: CHEMBL4095111
• Mol file: 63307-63-1.mol

Synonyms:2-Met-5-ProNH2-enkephalin;D-Met(2)-Pro(5)-enkephalinamide;enkephalin, Met(2)-ProNH2(5)-;enkephalin, methionyl(2)-prolinamide(5)-;GYKI 14238

Chemical Property of L-Tyrosyl-D-methionylglycyl-L-phenylalanyl-L-prolinamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1065°C at 760 mmHg
• Flash Point: 597.9°C
• PSA: 233.71000
• Density: 1.31g/cm³
• LogP: 4.12870
• XLogP3: 1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 612.27300419
• Heavy Atom Count: 43
• Complexity: 955

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)NCC(=O)NC(CC1=CC=CC=C1)C(=O)N2CCCC2C(=O)N)NC(=O)C(CC3=CC=C(C=C3)O)N
• Isomeric SMILES: CSCC[C@H](C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N2CCC[C@H]2C(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)O)N

Technology Process of L-Tyrosyl-D-methionylglycyl-L-phenylalanyl-L-prolinamide

There total 11 articles about L-Tyrosyl-D-methionylglycyl-L-phenylalanyl-L-prolinamide 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:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + 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) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6) → L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-L-proline amide (63307-63-1)

Guidance literature:

Fmoc-Pro-OH; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

With piperidine; In N,N-dimethyl-formamide;

N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH; Nα-fluorenyl-9-methoxycarbonyl-D-Met; Further stages;

DOI:10.1016/j.bmc.2017.02.052

Reference yield:

Boc Tyr D.Met Gly Phe Pro NH2 (66864-05-9) → L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-L-proline amide (63307-63-1)

Guidance literature:

With hydrogenchloride; acetic acid; In various solvent(s);

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-L-proline amide (63307-63-1)

Guidance literature:

Multi-step reaction with 5 steps

1: N-hydroxybenzotriazole, triethylamine, dicyclohexylcarbodiimide / dimethylformamide

2: HCl, acetic acid / various solvent(s) / 1.5 h

3: N-hydroxybenzotriazole, triethylamine, dicyclohexylcarbodiimide / dimethylformamide

4: NH₃ / methanol

5: HCl, acetic acid / various solvent(s)

With hydrogenchloride; ammonia; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

Boc Tyr D_.Met Gly Phe Pro NH₂

N-tert-butoxycarbonyl-L-phenylalanine

L-phenylalanine-L-proline methyl ester

t-butyloxycarbonyl-L-phenylalanyl-L-proline methyl ester