Imidazol-4-one-5-propionic acid is an intermediate in the metabolism of
histidine
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the de ...
. It is a colorless compound that is sensitive to light in air. The compound features an
imidazolone
Imidazolones are a family of heterocyclic compounds, the parents of which have the formula OC(NH)2(CH)2. Two isomers are possible, depending on the location of the carbonyl (CO) group. The NH groups are nonadjacent. A common route to imidazol-2 ...
ring.
Occurrence
It arises via the action of
urocanase
Urocanase (also known as imidazolonepropionate hydrolase or urocanate hydratase) is the enzyme () that catalyzes the second step in the degradation of histidine, the hydration of urocanate into imidazolonepropionate.
Urocanase is coded for by the ...
on
urocanic acid. Hydrolysis of the
heterocycle to the glutamic acid derivative is catalyzed by imidazolonepropionate hydrolase.
Microbial production of imidazol-4-one-5-propionic acid in the human gut has been shown to affect insulin signaling, which is relevant to
type II diabetes
Type 2 diabetes, formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, ...
.
See also
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Formiminoglutamic acid
Formiminoglutamic acid (FIGLU; conjugate base, formiminoglutamate) is an intermediate in the catabolism of L-histidine to L-glutamic acid. It thus is also a biomarker for intracellular levels of folate. The FIGLU test is used to identify vitam ...
*
Urocanate
Urocanic acid is an intermediate in the catabolism of L-histidine.
Metabolism
It is formed from L-histidine through the action of histidine ammonialyase (also known as histidase or histidinase) by elimination of ammonium.
In the liver, urocanic ...
*
Urocanate hydratase
Urocanase (also known as imidazolonepropionate hydrolase or urocanate hydratase) is the enzyme () that catalyzes the second step in the degradation of histidine, the hydration of urocanate into imidazolonepropionate.
Urocanase is coded for by the ...
References
Carboxylic acids
Imidazolines
Lactams
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