Tryptophan, N-indol-3-ylacetyl- (6CI)

Base Information

• Chemical Name: Tryptophan, N-indol-3-ylacetyl- (6CI)
• CAS No.: 57105-53-0
• Molecular Formula: C21H19 N3 O3
• Molecular Weight: 361.39
• Mol file: 57105-53-0.mol

Synonyms:L-Tryptophan,N-(1H-indol-3-ylacetyl)- (9CI); Tryptophan, N-indol-3-ylacetyl- (6CI)

Chemical Property of Tryptophan, N-indol-3-ylacetyl- (6CI)

Chemical Property:

• Vapor Pressure: 9.31E-25mmHg at 25°C
• Melting Point: 181-183 °C
• Boiling Point: 767.2°Cat760mmHg
• PKA: 3?+-.0.10(Predicted)
• Flash Point: 417.8°C
• PSA: 101.47000
• Density: 1.399g/cm³
• LogP: 3.84410

Purity/Quality:

98% ^*data from raw suppliers

Indole-3-acetyl-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Indole-3-acetyl-L-tryptophan is an indole-3-acetyl-amino acid conjugate involved in regulatory mechanisms for the control of auxin activity during physiological and pathophysiological responses. It may also be used in the synthesis of β-D-galactosidase and β-D-glucosidase inhibitors.

Technology Process of Tryptophan, N-indol-3-ylacetyl- (6CI)

There total 6 articles about Tryptophan, N-indol-3-ylacetyl- (6CI) 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: 95.0%

methyl (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoate → (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoic acid (57105-53-0)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1.5h;

DOI:10.1080/00397911.2019.1605446

Reference yield: 45.0%

1-(1H-benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanone (1080025-88-2) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoic acid (57105-53-0)

Guidance literature:

1-(1H-benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanone; L-Tryptophan; With triethylamine; In water; acetonitrile; at 20 ℃; for 1h;

With hydrogenchloride; In water; acetonitrile;

DOI:10.1021/jo8017796

Reference yield:

indole-3-acetic acid (87-51-4) + (S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoic acid (57105-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.25 h / Inert atmosphere

1.2: Inert atmosphere

2.1: sodium hydroxide

With 1,1'-carbonyldiimidazole; sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1007/s00044-014-1314-4

upstream raw materials:

indolyl acetyl chloride

L-Tryptophan

1-(1H-benzotriazol-1-yl)-2-(1H-indol-3-yl)ethanone

indole-3-acetic acid

Refernces

• 1、 Abu Khalaf, Reema,Abdula, Ahmed Mutanabbi,Mubarak, Mohammad S.,Taha, Mutasem O.. "Tryptophan and thiosemicarbazide derivatives: Design, synthesis, and biological evaluation as potential β-D-galactosidase and β-D-glucosidase inhibitors". . p. 2529 - 2550. Retrieved 2015/06/22.
• 2、 -. "Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same". . . Retrieved 2008/06/13.