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]
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| Names | |
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| IUPAC name
3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| MeSH | Imidazol-4-one-5-propionic+acid |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H8N2O3 | |
| Molar mass | 156.139 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence
editIt 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
editReferences
edit- ^ Hassall, H.; Greenberg, D. M. (1971). Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid. Methods Enzymol. Vol. 17(Pt. B). pp. 89–91. doi:10.1016/0076-6879(71)17014-0. ISBN 978-0-12-181877-7.
- ^ 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 (2018). "Microbially Produced Imidazole Propionate Impairs Insulin Signaling through mTORC1". Cell. 175 (4): 947–961.e17. doi:10.1016/j.cell.2018.09.055. PMID 30401435. S2CID 53229780.
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