Isoleucyl-Tryptophan

Base Information

• Chemical Name: Isoleucyl-Tryptophan
• CAS No.: 13589-06-5
• Molecular Formula: C₁₇H₂₃N₃O₃
• Molecular Weight: 317.388
• UNII: AY4YUP87RZ
• DSSTox Substance ID: DTXSID101029559
• Nikkaji Number: J587.917E
• Wikidata: Q4836115
• Metabolomics Workbench ID: 78853
• ChEMBL ID: CHEMBL56923
• Mol file: 13589-06-5.mol

Synonyms:H-ILE-TRP-OH;13589-06-5;Ile-Trp;BNC210;L-ISOLEUCYL-L-TRYPTOPHAN;Isoleucyl-Tryptophan;AY4YUP87RZ;L-Tryptophan, L-isoleucyl-;CHEMBL56923;CHEBI:74080;(S)-2-((2S,3S)-2-Amino-3-methylpentanamido)-3-(1H-indol-3-yl)Propanoic acid;(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid;L-Ile-L-Trp;L-Ile-L-Trp-OH;UNII-AY4YUP87RZ;IW-2143H-Ile-Trp-OH;SCHEMBL3512696;DTXSID101029559;IW;BDBM50407421;MFCD00190934;MS-24687;HY-105858;CS-0026797;S0552;F87777;Q4836115;(2S)-2-[[(2S,3S)-2-azaniumyl-3-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoate

Chemical Property of Isoleucyl-Tryptophan

Chemical Property:

• PSA: 108.21000
• LogP: 2.74440
• Storage Temp.: -15°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 317.17394160
• Heavy Atom Count: 23
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

H-Ile-Trp-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O)N
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O)N
• Recent ClinicalTrials: A Phase 2b Study of BNC210 Tablet Formulation in Adults With Post-Traumatic Stress Disorder (PTSD)
• Uses: H-ILE-TRP-OH maintains ACE inhibitory activity and may be used in the treatment of blood.

Technology Process of Isoleucyl-Tryptophan

There total 6 articles about Isoleucyl-Tryptophan 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:

Z-Ile-Trp-OH (196502-46-2) → Ile-Trp (13589-06-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1007/BF02524630

Reference yield:

(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-(1H-indol-3-yl)-propionic acid; compound with triethyl-amine → Ile-Trp (13589-06-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h;

DOI:10.1023/A:1012742917884

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → Ile-Trp (13589-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexylcarbodiimide; 1-hydroxybenzotriazole / dimethylformamide / 1 h / -5 - 0 °C

1.2: dimethylformamide / 16 h / 20 °C

2.1: 3.1 g / H₂ / 10 percent Pd/C / methanol / 4 h

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1023/A:1012742917884

upstream raw materials:

Z-Ile-Trp-OH

N-Cbz-L-Isoleucine

L-Tryptophan

L-isoleucine