| l-Kynurenine is a metabolite of the amino acid l-tryptophan used in the production of niacin.
Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation. Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response. Some cancers increase kynurenine production, which increases tumor growth.
Kynurenine protects the eye by absorbing UV light, especially in the UVA region (315–400 nm). Kynurenine is present in the lens and retina as one of multiple tryptophan derivatives produced in the eye, including 3-hydroxykynurenine, that together provide UV protection and aid in enhancing visual acuity. The use of kynurenine as a UV filter is consistent with its photostability and low photosensitization, owing to its efficient relaxation from the UV-induced excited state. The concentration of this UV filter decreases with age, and this loss of free kynurenine and the concomitant formation of relatively more photosensitizing kynurenine derivatives and kynurenine-protein conjugates may contribute to the formation of cataracts.
Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C. Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine. Blood levels of kynurenine are reduced in people with bipolar disorder. Kynurenine production is increased in Alzheimer's disease and cardiovascular disease where its metabolites are associated with cognitive deficits and depressive symptoms. Kynurenine is also associated with tics.
Kynureninase catalyzes the conversion of kynurenine into anthranilic acid while kynurenine-oxoglutarate transaminase catalyzes its conversion into kynurenic acid. Kynurenine 3-hydroxylase catalyzes the conversion of kynurenine to 3-hydroxykynurenine.
Kynurenine has also been identified as one of two compounds that makes up the pigment that gives the goldenrod crab spider its yellow color. |
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Read full article at Wikipedia
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| 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 |
| YGPSJZOEDVAXAB-QMMMGPOBSA-N |
| N[C@@H](CC(=O)c1ccccc1N)C(O)=O |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Saccharomyces cerevisiae
(NCBI:txid4932)
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Source: yeast.sf.net
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via kynurenine )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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View more via ChEBI Ontology
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3-(2-aminobenzoyl)-L-alanine
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(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
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IUPAC
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3-Anthraniloyl-L-alanine
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KEGG COMPOUND
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KYNURENINE
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PDBeChem
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L-Kynurenine
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KEGG COMPOUND
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2922-83-0
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CAS Registry Number
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KEGG COMPOUND
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2922-83-0
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CAS Registry Number
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ChemIDplus
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2942333
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Reaxys Registry Number
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Reaxys
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