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N'-Formylkynurenine

Chemical compound From Wikipedia, the free encyclopedia

N′-Formylkynurenine is an intermediate in the catabolism of tryptophan. It is a formylated derivative of kynurenine. The formation of N′-formylkynurenine is catalyzed by heme dioxygenases.[1]

Quick facts Names, Identifiers ...
N′-Formylkynurenine
Names
Systematic IUPAC name
(2S)-2-Amino-4-(2-formamidophenyl)-4-oxobutanoic acid
Other names
N′-Formyl-L-kynurenine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH N'-formylkynurenine
UNII
  • InChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)/t8-/m0/s1
    Key: BYHJHXPTQMMKCA-QMMMGPOBSA-N
  • C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)NC=O
Properties
C11H12N2O4
Molar mass 236.227 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis

The enzyme indoleamine 2,3-dioxygenase is the first and rate-limiting enzyme of tryptophan catabolism through the kynurenine pathway.[2]

 
O2
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 

Related enzymes performing a similar function are Indoleamine 2,3-dioxygenase 2 and tryptophan 2,3-dioxygenase.[3][4]

Metabolism

In the main sequence of the kynurenine pathway, the formyl group is removed by the enzyme arylformamidase, giving the compound after which the pathway is named:[5]

Alternatively, the enzyme kynureninase can produce N-formylanthranilic acid and L-alanine:[6][7]

 
H2O
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of Q27104373.
N-formylanthranilic acid
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