7-Azatryptophan

Base Information

• Chemical Name: 7-Azatryptophan
• CAS No.: 49758-35-2
• Molecular Formula: C10H11N3O2
• Molecular Weight: 205.216
• UNII: 72B59WRT3H
• DSSTox Substance ID: DTXSID40964394
• Nikkaji Number: J727.808J
• Wikidata: Q27466718
• Mol file: 49758-35-2.mol

Synonyms:7-azatryptophan;7-azatryptophan, (+-)-isomer;7-azatryptophan, (S)-isomer

Chemical Property of 7-Azatryptophan

Chemical Property:

• PSA: 92.00000
• LogP: 1.21760
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 205.085126602
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

99%+, ^*data from raw suppliers

(S)-2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2CC(C(=O)O)N)N=C1
• Isomeric SMILES: C1=CC2=C(NC=C2C[C@@H](C(=O)O)N)N=C1

Technology Process of 7-Azatryptophan

There total 8 articles about 7-Azatryptophan 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: 70.0%

C19H21N3O2 → (-)-(R)-7-azatryptophan (134235-82-8,1137-00-4) + (S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (49758-35-2,1137-00-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 8h; under 3040.2 Torr;

DOI:10.1002/bkcs.10287

Reference yield: 45.0%

Nα-Acetyl-DL-7-azatryptophan (63024-18-0) → (S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (49758-35-2,1137-00-4)

Guidance literature:

With sodium hydroxide; phosphate buffer; Aspergillus genus acylase; at 40 ℃; for 36h;

DOI:10.1016/S0957-4166(98)00130-X

Reference yield:

7-Azaindole (271-63-6) + L-serin (56-45-1,83245-15-2) → (S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (49758-35-2,1137-00-4)

Guidance literature:

With pyrococcus furiosus tryptophan synthase; In dimethyl sulfoxide; at 75 ℃; for 1h; pH=8; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1073/pnas.1516401112

upstream raw materials:

N^α-Acetyl-DL-7-azatryptophan

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate

2-fluoro-3-iodopyridine

7-Azaindole

Downstream raw materials:

2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethylamine

3-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile

C₂₂H₂₂N₆O

C₂₂H₂₁N₅O₂

Refernces

• 1、 Gee, Moon Bae,Kim, Tae Seung,Yum, Eul Kgun. "Palladium-catalyzed heteroannulation approach to 7-azatryptophan with a Sch?llkopf chiral auxiliary". . p. 1546 - 1549. Retrieved 2015/07/15.
• 2、 Lecointe,Rolland-Fulcrand,Roumestant,Viallefont,Martinez. "Chemoenzymatic synthesis of the two enantiomers of 7-azatryptophan". . p. 1753 - 1758. Retrieved 2007/10/03.