D-kynurenine

Names

[ Name ]:
D-kynurenine

[Synonym ]:
D-kynurenine
|A-Anthraniloyl-D-alanine
(2R)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
MFCD00133224
Benzenebutanoic acid, α,2-diamino-γ-oxo-, (αR)-
β-Anthraniloyl-D-alanine
D-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
(R)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid

Biological Activity

[Description]:

D-kynurenine, a metabolite of D-tryptophan, can serve as the bioprecursor of kynurenic acid (KYNA) and 3-hydroxykynurenine. D-Kynurenine is an agonist for G protein-coupled receptor, GPR109B. D-Kynurenine is a substrate in a fluorometric assay of D-amino acid oxidase. D-kynurenine promotes epithelial-to-mesenchymal transition via activating aryl hydrocarbon receptor (AHR)[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> Aryl Hydrocarbon Receptor

[Target]

Human Endogenous Metabolite

[In Vitro]

D-kynurenine (10, 40, 60, and 100 µM) positively regulates the metastasis of 95D cells, a lung cancer cell line, which is reduced upon siRNAAhr treatment. Significant enhancement VIM expression was detected in the presence of D-kynurenine (10 and 40 µM). 10 µM D-kynurenine markedly attenuates E-cadherin level. 10 µM D-kynurenine-mediated changes of VIM and E-cadherin are substantially attenuated on siRNAAhr treatment as well. The evidences-10/40 µM D-kynurenine-induced up-regulation of CYP1A1, 10 µM D-kynurenine-induced increase of nuclear transfer of Ahr, and 10/40/60/100 µM D-kynurenine-induced enhancement of DER-luciferase activity-indicated that D-kynurenine Is capable of activating Ahr in fact[4].

[References]

[1]. Wang XD, et al. A method for the determination of D-kynurenine in biological tissues. Anal Bioanal Chem. 2013 Dec;405(30):9747-54.

[2]. Irukayama-Tomobe Y, et al. Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3930-4.

[3]. Kozaki A, et al. Fluorimetric assay for D-amino acid oxidase activity in rat brain homogenate by using D-kynurenine as a substrate. Biosci Trends. 2012 Oct;6(5):241-7.

[4]. Duan Z, et al. Promoting epithelial-to-mesenchymal transition by D-kynurenine via activating aryl hydrocarbon receptor. Mol Cell Biochem. 2018 Nov;448(1-2):165-173.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
466.6±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₂N₂O₃

[ Molecular Weight ]:
208.214

[ Flash Point ]:
236.0±28.7 °C

[ Exact Mass ]:
208.084793

[ PSA ]:
106.41000

[ LogP ]:
1.09

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.626

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B.

Proc. Natl. Acad. Sci. U. S. A. 106 , 3930-3934, (2009)

GPR109B (HM74) is a putative G protein-coupled receptor (GPCR) whose cognate ligands have yet to be characterized. GPR109B shows a high degree of sequence similarity to GPR109A, another GPCR that was ...

Purification and biochemical characterization of some of the properties of recombinant human kynureninase.

Eur. J. Biochem. 269 , 2069-2074, (2002)

Recombinant human kynureninase (L-kynurenine hydrolase, EC 3.7.1.3) was purified to homogeneity (60-fold) from Spodoptera frugiperda (Sf9) cells infected with baculovirus containing the kynureninase g...

Changes in the plasma concentrations of D-kynurenine and kynurenic acid in rats after intraperitoneal administration of tryptophan enantiomers.

Chirality 22 , 901-916, (2010)

An aqueous solution of enantiomerically pure tryptophan (Trp), namely, D-Trp or L-Trp (100 mg/kg), was administered intraperitoneally to male Sprague-Dawley rats. The time-course profiles of the rat p...