Imidazol-4-one-5-propionic acid
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IUPAC name 3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid | |
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ChemSpider |
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MeSH | Imidazol-4-one-5-propionic+acid |
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InChI
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Properties | |
Chemical formula | 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). N verify (what is YN ?) Infobox references |
Chemical compound
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
- ^ 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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lysine→ | |
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leucine→ | |
tryptophan→alanine→ |
G→pyruvate→ citrate |
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G→glutamate→ α-ketoglutarate |
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G→propionyl-CoA→ succinyl-CoA |
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G→fumarate |
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G→oxaloacetate |
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Cysteine metabolism |
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