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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 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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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)
Novel protein modification by kynurenine in human lenses.
Vazquez S
The Journal of Biological Chemistry, 277(7), 4867-4873 (2002)
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