Imidazol-4-one-5-propionic acid explained

Imidazol-4-one-5-propionic acid is an intermediate in the metabolism of histidine. It is a colorless compound that is sensitive to light in air. The compound features an imidazolone ring.^[1]

Occurrence

It arises via the action of urocanase 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.^[2]

See also

• Formiminoglutamic acid
• Urocanate
• Urocanate hydratase

References

1. Book: Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid. Hassall, H.. Greenberg, D. M.. Methods Enzymol.. 1971. 17(Pt. B). 89–91. 10.1016/0076-6879(71)17014-0. 978-0-12-181877-7 .
2. 10.1016/j.cell.2018.09.055. Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1. 2018. Koh. Ara. Molinaro. Antonio. Ståhlman. Marcus. Khan. Muhammad Tanweer. Schmidt. Caroline. Mannerås-Holm. Louise. Wu. Hao. Carreras. Alba. Jeong. Heeyoon. Olofsson. Louise E.. Bergh. Per-Olof. Gerdes. Victor. Hartstra. Annick. De Brauw. Maurits. Perkins. Rosie. Nieuwdorp. Max. Bergström. Göran. Bäckhed. Fredrik. Cell. 175. 4. 947–961.e17. 30401435. 53229780. free.