L-KYNURENINE

Base Information

• Chemical Name: L-KYNURENINE
• CAS No.: 2922-83-0
• Molecular Formula: C10H12N2O3
• Molecular Weight: 208.217
• Hs Code.: 2922509090
• Mol file: 2922-83-0.mol

Synonyms:Alanine,3-anthraniloyl-, L- (8CI);Benzenebutanoic acid, α,2-diamino-γ-oxo-, (S)-;L-3-(o-Aminobenzoyl)alanine;L-Kynurenine;

Chemical Property of L-KYNURENINE

Chemical Property:

• Appearance/Colour: light yellow crystalline
• Melting Point: 219℃ (decomposition) (ethanol )
• Refractive Index: -33 ° (C=0.4, H2O)
• Boiling Point: 466.6 °C at 760 mmHg
• PKA: 2.21±0.23(Predicted)
• Flash Point: 236 °C
• PSA: 106.41000
• Density: 1.343 g/cm³
• LogP: 1.53500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Soluble in DMSO (up to 2 mg/ml) or in Water (up to 2 mg/ml).
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 208.08479225
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

L-Kynurenine ^*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=CC=C(C(=C1)C(=O)CC(C(=O)[O-])[NH3+])N
• Isomeric SMILES: C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)[O-])[NH3+])N
• Description: Kynurenine (2922-83-0) is a tryptophan catabolite.1?Endogenous tumor-promoting ligand of the human aryl hydrocarbon receptor (AhR). Constitutively generated by human tumor cells via the action of the tryptophan degrading enzyme, tryptophan-2,3-dioxygenase (TDO). Kynurenine suppresses antitumor immune responses and promotes tumor cell survival and motility.2
• Uses: L-Kynurenine has been used as a standard for indoleamine-2,3-dioxygenase (IDO) assay. It has also been used as a standard to extract and quantify kynurenine from cultured cells and media.

Technology Process of L-KYNURENINE

There total 18 articles about L-KYNURENINE 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%

(2S)-Methyl 2-(N-tert-butoxycarbonylamino)-4-oxo-4-(2'-aminophenyl)butanoate (172479-59-3) → L-kynurenine (2922-83-0)

Guidance literature:

With hydrogen bromide; acetic acid; methyloxirane; 1.) r.t., 20 min, 2.) i-PrOH;

DOI:10.1039/a606394b

Reference yield: 62.0%

2-tert-butoxycarbonylamino-4-(2-tert-butoxycarbonylamino-phenyl)-4-oxo-butyric acid tert-butyl ester → L-kynurenine (2922-83-0)

Guidance literature:

With trifluoroacetic acid; In chloroform; Heating;

DOI:10.1016/S0040-4039(03)01017-7

Reference yield: 61.0%

oxindolylalanine (32999-55-6) → L-kynurenine (343-65-7,2922-83-0,3039-10-9,13441-51-5)

Guidance literature:

at 50 - 60 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)98249-2

upstream raw materials:

L-Tryptophan

L-Kynurenine dihydrobromide

(2S)-Methyl 2-(N-tert-butoxycarbonylamino)-4-oxo-4-(2'-aminophenyl)butanoate

2-iodophenylamine

Downstream raw materials:

(2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid

(2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid

N^α-t-butyloxycarbonyl-L-kynurenine

Kynurenic acid methyl ester

Refernces

• 1、 Hamdy, Mohamed S.,Scott, Elinor L.,Carr, Robert H.,Sanders, Johan P. M.. "A novel photocatalytic conversion of tryptophan to kynurenine using black light as a light source". . p. 338 - 344. Retrieved 2012.
• 2、 Lu, Changyuan,Lin, Yu,Yeh, Syun-Ru. "Spectroscopic studies of ligand and substrate binding to human indoleamine 2,3-dioxygenase". . p. 5028 - 5034. Retrieved 2010.
• 3、 Henrottin, Jean,Zervosen, Astrid,Lemaire, Christian,Sapunaric, Frédéric,Laurent, Sophie,Van Den Eynde, Benoit,Goldman, Serge,Plenevaux, Alain,Luxen, André. "N 1-fluoroalkyltryptophan analogues: Synthesis and in vitro study as potential substrates for indoleamine 2,3-dioxygenase". supporting information. p. 260 - 265. Retrieved 2015/03/30.