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K8625

Sigma-Aldrich

L-Kynurenine

≥98% (HPLC)

Synonym(s):

β-Anthraniloyl-L-alanine, L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid

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About This Item

Empirical Formula (Hill Notation):
C10H12N2O3
CAS Number:
2922-83-0
Molecular Weight:
208.21
MDL number:
MFCD00069912
UNSPSC Code:
12352209
PubChem Substance ID:
24896246
NACRES:
NA.26

product name

L-Kynurenine, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

mp

219 °C

application(s)

detection

SMILES string

N[C@@H](CC(=O)c1ccccc1N)C(O)=O

InChI

1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

InChI key

YGPSJZOEDVAXAB-QMMMGPOBSA-N

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Application

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.

Biochem/physiol Actions

L-Kynurenine is a key intermediate in the breakdown of L-tryptophan and the formation of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. It is involved in a variety of neurological processes and diseases. L-Kynurenine is a substrate for kynureninase/kynurenine hydrolase; kynurenine 3-monooxygenase and kynurenine-oxoglutarate transaminase.
Key intermediate in the breakdown pathway of tryptophan.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extraction and Quantification of Tryptophan and Kynurenine from Cultured Cells and Media Using a High Performance Liquid Chromatography (HPLC) System Equipped with an Ultra-Sensitive Diode Array Detector
Jeffrey Kim
Bio-protocol, 6(7), e1781-e1781 (2016)
Essential and Non-Essential Metals Metabolites with Antibiotic Activity Pharmacology of Benzodiazepines Interferon Gamma Research (2012)
Linnéa Asp et al.
Journal of inflammation (London, England), 8, 25-25 (2011-10-11)
The kynurenine pathway (KP) is the main route of tryptophan degradation in the human body and generates several neuroactive and immunomodulatory metabolites. Altered levels of KP-metabolites have been observed in neuropsychiatric and neurodegenerative disorders as well as in patients with
Kimberley Kolijn et al.
Cancer research, 78(16), 4671-4679 (2018-06-21)
Cancer invasion and metastasis are driven by epithelial-mesenchymal transition (EMT), yet the exact mechanisms that account for EMT in clinical prostate cancer are not fully understood. Expression of N-cadherin is considered a hallmark of EMT in clinical prostate cancer. In
Evaluation of radiofluorinated carboximidamides as potential IDO-targeted PET tracers for cancer imaging
Xuan Huang
Oncotarget, 8(29), 46900-46914 (2017)
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