2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

Base Information

• Chemical Name: 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid
• CAS No.: 7303-50-6
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.216
• Hs Code.: 2933998090
• European Community (EC) Number: 672-717-2
• NSC Number: 19495
• UNII: 26NJJ3M0J5
• DSSTox Substance ID: DTXSID101229652
• Nikkaji Number: J207.917H
• Mol file: 7303-50-6.mol

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

Chemical Property of 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

Chemical Property:

• Appearance/Colour: White Powder
• Melting Point: 275°C dec.
• Boiling Point: 466.1 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 235.7 °C
• PSA: 105.13000
• Density: 1.434 g/cm³
• LogP: 2.05270
• Storage Temp.: −20°C
• 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:

98% ^*data from raw suppliers

DL-7-Azatryptophan Monohydrate >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2CC(C(=O)O)N)N=C1
• Uses: DL-7-Azatryptophan is an unusual alpha-amino acid with a very potent fluorescent activity. Its used as a vehicle for probing the structure and dynamics of protein and peptides

Technology Process of 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

There total 6 articles about 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid 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: 75.0%

ethyl 2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate → 7-azatryptophan (7303-50-6,1137-00-4)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1074/jbc.M116.741561

Reference yield: 72.5%

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate (211179-97-4) → 7-azatryptophan (7303-50-6,1137-00-4)

Guidance literature:

With hydrogenchloride; In water; for 15h; Reflux;

Reference yield:

7-azagramine (5654-92-2) → 7-azatryptophan (7303-50-6,1137-00-4)

Guidance literature:

Multi-step reaction with 2 steps

2: concentrated aqueous HCl

With hydrogenchloride;

DOI:10.1021/ja01607a071

upstream raw materials:

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

7-azagramine

7-Azaindole

N,N,N-trimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanaminium iodide

Downstream raw materials:

(-)-(R)-7-azatryptophan

(S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid

C₂₅H₂₁N₃O₄

(5aR,10R)-10-benzo[1,3]dioxol-5-yl-7-[(R)-1-benzylpyrrolidin-3-yl]-5,5a,7,8,10,11-hexahydro-1,7,9a,11-tetraaza-benzo[b]fluorene-6,9-dione

Refernces

• 1、 Füller, Janis J.,R?pke, René,Krausze, Joern,Rennhack, Kim E.,Daniel, Nils P.,Blankenfeldt, Wulf,Schulz, Stefan,Jahn, Dieter,Moser, Jürgen. "Biosynthesis of violacein, structure and function of L-tryptophan oxidase VioA from chromobacterium violaceum". . p. 20068 - 20084. Retrieved 2016/11/05.