5-Oxoprolyltryptophan

Base Information

• Chemical Name: 5-Oxoprolyltryptophan
• CAS No.: 35937-24-7
• Molecular Formula: C16H17 N3 O4
• Molecular Weight: 315.32
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00189501
• Nikkaji Number: J550.035D
• Wikidata: Q83061610
• Mol file: 35937-24-7.mol

Synonyms:5-O-Pro-Trp;5-oxo-L-prolyltryptophan;5-oxoprolyltryptophan

Chemical Property of 5-Oxoprolyltryptophan

Chemical Property:

• Vapor Pressure: 2.82E-25mmHg at 25°C
• Boiling Point: 775°Cat760mmHg
• Flash Point: 422.5°C
• PSA: 118.27000
• Density: 1.417g/cm³
• LogP: 1.67460
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 315.12190603
• Heavy Atom Count: 23
• Complexity: 496

Purity/Quality:

99%+, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O

Technology Process of 5-Oxoprolyltryptophan

There total 5 articles about 5-Oxoprolyltryptophan 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: 45.0%

L-pyroglutamyl-L-tryptophan ethyl ester (87694-58-4) → L-pyroglutamyl-L-tryptophan (35937-24-7)

Guidance literature:

With sodium hydroxide; In water; Ambient temperature;

Reference yield:

L-tryptophan ethyl ester hydrochloride (2899-28-7,6519-67-1,61535-49-7,67557-18-0,68401-14-9) → L-pyroglutamyl-L-tryptophan (35937-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, ethyl chloroformate, 2.) triethylamine / 1.) THF, 0 deg C, 30 min, 2.) r.t., 3 h

2: 93 percent / H₂ / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature

3: 45 percent / NaOH / H₂O / Ambient temperature

With sodium hydroxide; hydrogen; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In methanol; water;

Reference yield:

L-Pyroglutamic acid (98-79-3) → L-pyroglutamyl-L-tryptophan (35937-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / triethylamine, dicyclohexylcarbodiimide / dimethylformamide / 16 h / Ambient temperature

2: 45 percent / NaOH / H₂O / Ambient temperature

With sodium hydroxide; triethylamine; dicyclohexyl-carbodiimide; In water; N,N-dimethyl-formamide;

upstream raw materials:

L-pyroglutamyl-L-tryptophan ethyl ester

Cbz-L-pGlu-OH

L-tryptophan ethyl ester hydrochloride

N-carbobenzoxy-L-pyroglutamyl-L-tryptophan ethyl ester

Refernces