Imidazol-4-one-5-propionic acid

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]

Imidazol-4-one-5-propionic acid
Names
IUPAC name
3-(5-Oxo-1,4-dihydroimidazol-4-yl)propanoic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH Imidazol-4-one-5-propionic+acid
  • InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11) ☒N
    Key: HEXMLHKQVUFYME-UHFFFAOYSA-N ☒N
  • InChI=1/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)
    Key: HEXMLHKQVUFYME-UHFFFAOYAX
  • O=C1N\C=N/C1CCC(=O)O
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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Infobox references

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

References
  1. Hassall, H.; Greenberg, D. M. (1971). "Preparation and properties of 4(5)-imidazolone-5(4)-propionic acid". Methods Enzymol. 17(Pt. B): 89–91. doi:10.1016/0076-6879(71)17014-0.
  2. 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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