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K3750

Sigma-Aldrich

L-Kynurenine sulfate salt

≥98% (HPLC), suitable for ligand binding assays

Synonym(s):

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

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About This Item

Linear Formula:
C10H12N2O3 · H2SO4
CAS Number:
16055-80-4
Molecular Weight:
306.29
MDL number:
MFCD00039104
UNSPSC Code:
12352209
PubChem Substance ID:
24896233
NACRES:
NA.26

product name

L-Kynurenine sulfate salt, crystalline

assay

≥98% (HPLC)

form

crystalline

technique(s)

ligand binding assay: suitable

color

light yellow

storage temp.

−20°C

SMILES string

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

InChI

1S/C10H12N2O3.H2O4S/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15;1-5(2,3)4/h1-4,8H,5,11-12H2,(H,14,15);(H2,1,2,3,4)/t8-;/m0./s1

InChI key

KAXRWMOLNJZCEW-QRPNPIFTSA-N

Application

L-Kynurenine sulfate salt has been used as a substrate to study the enzyme activity of kynurenine aminotransferase. It has also been used in the synthesis of Kyn adducts of certain amino acids .

Biochem/physiol Actions

L-Kynurenine (L-Kyn) is a precursor of kynurenic acid which is the only recognized endogenous excitatory amino acid receptor antagonist in the central nervous system. L-Kyn is known to be a pigment generating component in animals. In mammals, it modulates the transmission of glutamate neurotransmitter. It is also considered to be a sex-attracting pheromone in vertebrates.
L-Kynurenine is a key intermediate in the breakdown of L-tryptophan and the formation of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. L-kynurenine 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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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L-Kynurenine, an amino acid identified as a sex pheromone in the urine of ovulated female masu salmon.
Yambe H
Proceedings of the National Academy of Sciences of the USA, 103(42), 15370-15374 (2006)
K Nagy et al.
Bioorganic & medicinal chemistry, 19(24), 7590-7596 (2011-11-15)
The overactivation of excitatory amino acid receptors plays a key role in the pathomechanism of several neurodegenerative disorders and in ischemic and post-ischemic events. Kynurenic acid (KYNA) is an endogenous product of the tryptophan metabolism and, as a broad-spectrum antagonist
Mitochondrial aspartate aminotransferase: a third kynurenate-producing enzyme in the mammalian brain.
Guidetti P
Journal of Neurochemistry, 102(1), 103-111 (2007)
Neuroprotective effects of L-kynurenine on hypoxia-ischemia and NMDA lesions in neonatal rats.
Nozaki K and Beal MF
Journal of Cerebral Blood Flow and Metabolism, 12(3), 400-407 (1992)
Klas Linderholm et al.
International journal of tryptophan research : IJTR, 3, 1-12 (2010-01-01)
Kynurenic acid (KYNA) is an endogenous metabolite of tryptophan. Studies have revealed increased brain KYNA levels in patients with schizophrenia. Prepulse inhibition (PPI) is a behavioral model for sensorimotor gating and found to be reduced in schizophrenia. Previous studies have
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