Azatyrosine

Base Information

• Chemical Name: Azatyrosine
• CAS No.: 58525-82-9
• Molecular Formula: C₈H₁₀N₂O₃
• Molecular Weight: 182.179
• UNII: 0XTS2H0JH1
• Nikkaji Number: J14.678A
• Wikidata: Q27231231
• Metabolomics Workbench ID: 99747
• Mol file: 58525-82-9.mol

Synonyms:azatyrosine;beta-(5-hydroxy-2-pyridyl)alanine;beta-(5-hydroxy-2-pyridyl)alanine, (S)-isomer;SF 1346

Chemical Property of Azatyrosine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 358.2°Cat760mmHg
• PKA: 1.68±0.10(Predicted)
• Flash Point: 170.4°C
• PSA: 96.44000
• Density: 1.324g/cm³
• LogP: 0.44190
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 182.06914219
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

99%min ^*data from raw suppliers

L-Azatyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1O)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=NC=C1O)C[C@@H](C(=O)O)N

Technology Process of Azatyrosine

There total 25 articles about Azatyrosine 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: 90.0%

Phenylmethyl 2(S)-<<<(1,1-dimethylethyl)oxy>carbonyl>amino>-3-<5'-methoxy-2'-pyridyl>propionate → L-azatyrosine (58525-82-9,185389-91-7)

Guidance literature:

With boron tribromide; In dichloromethane; 1.) -78 deg C, 20 min, 2.) r.t., overnight;

DOI:10.1021/jo00113a056

Reference yield: 85.0%

(S)-2-Acetylamino-3-(5-hydroxy-pyridin-2-yl)-propionic acid ethyl ester → L-azatyrosine (58525-82-9,185389-91-7)

Guidance literature:

With hydrogenchloride; for 3.5h; Heating;

DOI:10.1016/0960-894X(96)00480-5

Reference yield: 65.0%

methyl (2S)-2-amino-3-(5-benzenesulfonyloxypyridin-2-yl)propanoate (663604-04-4) → L-azatyrosine (58525-82-9,185389-91-7)

Guidance literature:

With sodium hydroxide; for 6h; Heating;

DOI:10.3987/com-03-s39

upstream raw materials:

<-2S>-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl 2-amino-3-(2-(5-benzenesulfonyloxy)pyridyl)propionamide

2-hydroxypyridin

2-oxo-propionic acid

methyl (2S)-2-amino-3-(5-benzenesulfonyloxypyridin-2-yl)propanoate

Downstream raw materials:

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(5-hydroxy-pyridin-2-yl)-propionic acid

Refernces

• 1、 Cremonesi, Giuseppe,Dalla Croce, Piero,La Rosa, Concetta,Pizzatti, Enrica. "A stereocontrolled synthesis of (R)- and (S)-azatyrosine". . p. 563 - 567. Retrieved 2007/10/03.
• 2、 Adamczyk,Akireddy,Reddy. "Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine.". . p. 3157 - 3159. Retrieved 2007/10/03.