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:

≥98% ^*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
• General Description: **L-KYNURENINE** is a key intermediate in the kynurenine pathway, serving as a precursor for the synthesis of 3-hydroxykynurenine and other metabolites. In the context of this study, L-kynurenine was used as a substrate or reference compound in the LC-MS/MS assay to evaluate the activity of Anopheles gambiae 3-hydroxykynurenine transaminase (Ag-HKT) and assess potential inhibitors. Its role highlights its importance in mosquito physiology and as a potential target for disrupting malaria transmission through enzymatic inhibition. **Return:** L-KYNURENINE is a metabolic precursor in the kynurenine pathway, playing a role in enzymatic processes relevant to mosquito physiology and serving as a reference compound in studies targeting malaria transmission-blocking strategies.

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:

L-alanin

2-amino-4-(2-amino-phenyl)-4-hydroxy-butyric acid

N^α-t-butyloxycarbonyl-L-kynurenine

kynuramine

Refernces

Study of Anopheles gambiae 3-hydroxykynurenine transaminase activity and inhibition by LC-MS/MS method

10.1016/j.jpba.2019.05.025

The study focuses on the activity and inhibition of Anopheles gambiae 3-hydroxykynurenine transaminase (Ag-HKT), an enzyme that metabolizes 3-hydroxykynurenine into xanthurenic acid, which is crucial for mosquito vector physiology and a potential target for transmission-blocking drugs and insecticides. The researchers developed and validated a new LC-MS/MS method to evaluate Ag-HKT activity and the potency of inhibitors. Chemicals used in the study included L-kynurenine (L-KYN), kynurenic acid (KA), xanthurenic acid (XA), 3-hydroxy-DL-kynurenine (D,L-3-HK), and pyridoxal 5′-phosphate (PLP) as key components of the enzymatic assay. Additionally, 4-(2-aminophenyl)-4-oxobutanoic acid (INI) and its derivative 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid (3-OH-INI) were synthesized and tested as potential inhibitors of Ag-HKT. The purpose of these chemicals was to establish a method for quantifying the enzyme's activity and to identify and characterize compounds that could inhibit Ag-HKT, providing a basis for the development of new insecticides and malaria transmission-blocking drugs.

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