Cholecystokinin hexapeptide

Base Information

• Chemical Name: Cholecystokinin hexapeptide
• CAS No.: 21163-42-8
• Molecular Formula: C36H48N8O8S2
• Molecular Weight: 784.9451
• DSSTox Substance ID: DTXSID20175401
• Nikkaji Number: J2.007.457D
• Wikidata: Q83045731
• Mol file: 21163-42-8.mol

Synonyms:CCK-6;cholecystokinin hexapeptide;cholecystokinin hexapeptide sulfate (1:1);Met-Gly-Trp-Met-Asp-Phe-NH2;methionyl-glycyl-tryptophyl-methionyl-aspartyl-phenylalaninamide

Chemical Property of Cholecystokinin hexapeptide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1282.9°Cat760mmHg
• Flash Point: 729.7°C
• PSA: 336.74000
• Density: 1.343g/cm³
• LogP: 5.85350
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 23
• Exact Mass: 784.30365287
• Heavy Atom Count: 54
• Complexity: 1290

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)NCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N)N
• Isomeric SMILES: CSCC[C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)N

Technology Process of Cholecystokinin hexapeptide

There total 11 articles about Cholecystokinin hexapeptide 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:

tert-butyloxycarbonylmethionyl-glycyl-tryptophyl-methionyl-aspartyl-phenylalanine amide (23446-11-9) → H-Met-Gly-Trp-Met-Asp-Phe-NH2 (CCK-6) (21163-42-8)

Guidance literature:

With methyl-phenyl-thioether; trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1248/cpb.34.115

Reference yield:

2-((2S)-2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanamido)acetic acid (23446-03-9) → H-Met-Gly-Trp-Met-Asp-Phe-NH2 (CCK-6) (21163-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 15.2 g / DCC / dimethylformamide / 1.) 0 deg C, 2 h; 2.) 7-8 deg C, overnight

2: 1.) NEt₃; 2.) HOBt / 1.) DMF, 10 min; 2.) 7-8 deg C, overnight

3: TFA, thioanisole / 1 h / 0 °C

With methyl-phenyl-thioether; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.115

Reference yield:

Boc-Met-OTcp (16948-13-3) → H-Met-Gly-Trp-Met-Asp-Phe-NH2 (CCK-6) (21163-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 75.5 percent / Et₃N / H₂O / Ambient temperature

2: 15.2 g / DCC / dimethylformamide / 1.) 0 deg C, 2 h; 2.) 7-8 deg C, overnight

3: 1.) NEt₃; 2.) HOBt / 1.) DMF, 10 min; 2.) 7-8 deg C, overnight

4: TFA, thioanisole / 1 h / 0 °C

With methyl-phenyl-thioether; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.115

upstream raw materials:

tert-butyloxycarbonylmethionyl-glycyl-tryptophyl-methionyl-aspartyl-phenylalanine amide

N-tert-butoxycarbonyl-L-methionine

N-tert-butoxycarbonyl-L-phenylalanine

N-(tert-Butoxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine

Downstream raw materials:

Boc-Tyr(SO₃Na)-Met-Gly-Trp-Met-Asp-Phe-NH₂ (Boc-CCK-7)

β-(4-hydroxyphenyl)propionyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide