Tyrosyl-glycyl-phenylalanyl-glycyl-glycine

Base Information

• Chemical Name: Tyrosyl-glycyl-phenylalanyl-glycyl-glycine
• CAS No.: 105250-85-9
• Molecular Formula: C₂₄H₂₉N₅O₇
• Molecular Weight: 499.524
• DSSTox Substance ID: DTXSID10909398
• Wikidata: Q82879004
• ChEMBL ID: CHEMBL43978
• Mol file: 105250-85-9.mol

Synonyms:historphin;OGP(10-14);osteogenic growth peptide (10-14);Tyr-Gly-Phe-Gly-Gly;tyrosyl-glycyl-phenylalanyl-glycyl-glycine

Chemical Property of Tyrosyl-glycyl-phenylalanyl-glycyl-glycine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1028°Cat760mmHg
• Flash Point: 575.5°C
• PSA: 199.95000
• Density: 1.352g/cm³
• LogP: 0.68660
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 499.20669828
• Heavy Atom Count: 36
• Complexity: 764

Purity/Quality:

99%+, ^*data from raw suppliers

OsteogenicGrowthPeptide10-14 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)NCC(=O)NCC(=O)O)NC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)NCC(=O)NCC(=O)O)NC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N

Technology Process of Tyrosyl-glycyl-phenylalanyl-glycyl-glycine

There total 11 articles about Tyrosyl-glycyl-phenylalanyl-glycyl-glycine 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: 58.9%

[2-((S)-2-{2-[(S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-acetylamino}-3-phenyl-propionylamino)-acetylamino]-acetic acid ethyl ester → historphine (105250-85-9)

Guidance literature:

With methyl-phenyl-thioether; hydrogen bromide; Ambient temperature;

Reference yield:

Boc-Tyr(Bzl)-Gly-Phe-OH → historphine (105250-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 77.9 percent / N-hydroxysuccinimide, triethylamine, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 2 h / -10 °C

2: 58.9 percent / 36percent aq. HBr, thioanisole / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; methyl-phenyl-thioether; hydrogen bromide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

Fmoc-Tyr(tBu)-Gly-OSu → historphine (105250-85-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / water; tetrahydrofuran / 25 °C / Large scale

2: dicyclohexyl-carbodiimide / tetrahydrofuran / 12 h / 20 °C / Cooling with ice; Large scale

3: sodium hydrogencarbonate / water; tetrahydrofuran / 8 h / 20 °C / Large scale

4: piperidine / 1,4-dioxane / 1 h / Large scale

5: trifluoroacetic acid; water / 1 h

With piperidine; water; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/acs.oprd.5b00004

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-Fmoc L-Phe

Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(tBu)-OSu

Refernces

• 1、 Ma, Manlung,Kuang, Yi,Gao, Yuan,Zhang, Yan,Gao, Ping,Xu, Bing. "Aromatic-aromatic interactions induce the self-assembly of pentapeptidic derivatives in water to form nanofibers and supramolecular hydrogels". supporting information; experimental part. p. 2719 - 2728. Retrieved 2010/05/01.