175777-22-7

Basic information

• Product Name: (R)-4-Chlorokynurenine
• Synonyms: (R)-4-Chlorokynurenine
• CAS NO: 175777-22-7
• Molecular Formula: C10H11ClN2O3
• Molecular Weight: 242.65894
• Product Categories: Amino Acids & Derivatives, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 175777-22-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-4-Chlorokynurenine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-Chlorokynurenine(175777-22-7)
• EPA Substance Registry System: (R)-4-Chlorokynurenine(175777-22-7)

Safety Data

• Hazardous Substances Data: 175777-22-7(Hazardous Substances Data)

Usage

Uses

(R)-4-Chlorokynurenine, is a derivative of Kynurenine (K661000), which is a tryptophan metabolite, and a precursor of Kynurenic Acid (K660500), having antiexcitotoxic and anticonvulsant properties.

Upstream product

• 108-42-9 3-chloro-aniline 
• 64605-37-4 1-(2-amino-4-chlorophenyl)-2-chloroethan-1-one 
• 73-22-3 L-Tryptophan 
• 33468-35-8 6-chloro-DL-tryptophan 
• 153042-33-2 tert-butyl (5-chloro-2-iodophenyl)carbamate 
• 89-63-4 4-Chloro-2-nitroaniline 
• 6828-35-9 5-chloro-2-iodoaniline 
• 5446-05-9 4-chloro-2-nitroiodobenzene 
• 153042-35-4 (S)-4-[2-(2-Amino-4-chloro-phenyl)-2-oxo-ethyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides

4-Chloro-l-kynurenine (3-(4-chloroanthraniloyl)-l-alanine, l-4-ClKyn), an amino acid known as a prospective antidepressant, was recently for the first time found in nature in the lipopeptide antibiotic taromycin. Here, we report another instance of its identification in a natural product: 4-chloro-l-kynurenine was isolated from acidic hydrolysis of a new complex peptide antibiotic INA-5812. l-4-ClKyn is a fluorescent compound responsible for the fluorescence of the above antibiotic. Whereas fluorescence of 4-chlorokynurenine was not reported before, we synthesized the racemic compound and studied its emission in various solvents. Next, we prepared conjugates of dl-4-ClKyn with two suitable energy acceptors, BODIPY FL and 3-(phenylethynyl)perylene (PEPe), and studied fluorescence of the derivatives. 4-Chloro-dl-kynurenine emission is not detected in both conjugates, thus evidencing effective energy transfer. However, BODIPY FL emission in the conjugate is substantially reduced, probably due to collisional or photoinduced charge-transfer-mediated quenching. The intrinsic fluorescence of l-4-ClKyn amino acid in antibiotics paves the way for spectral studies of their mode of action.

SYNTHESIS OF 4-CHLOROKYNURENINES AND INTERMEDIATES

The invention relates to an overall enantio-specific synthesis of 4-chlorokynurenine compounds, in particular L-4-chlorokynurenine, with improved yields. Large-scale syntheses are disclosed. The invention also relates to novel intermediates in the synthes

SYNTHESIS OF CHIRAL KYNURENINE COMPOUNDS AND INTERMEDIATES

Provided are methods for the synthesis of compounds including chiral kynurenine compounds, intermediates useful for the synthesis thereof, and related compounds. For example, methods are provided for the synthesis of L-4-chlorokynurenine.