2-Oxohistidine

2-Oxohistidine
Names
	IUPAC name 3-(2-Oxo-2H-imidazol-4-yl)alanine
Identifiers
CAS Number	181996-08-7;
3D model (JSmol)	Interactive image;
ChemSpider	19981749;
PubChem CID	127761;
CompTox Dashboard (EPA)	DTXSID20934257 ;
	InChI InChI=1S/C6H7N3O3/c7-4(5(10)11)1-3-2-8-6(12)9-3/h2,4H,1,7H2,(H,10,11) COPY Key: MWUSZYAURGSGRY-UHFFFAOYSA-N;
	SMILES C1=NC(=O)N=C1CC(C(=O)O)N;
Properties
Chemical formula	C6H7N3O3
Molar mass	169.140 g·mol−1
Appearance	white solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Oxohistidine is a derivative of histidine damaged by reactive oxygen species. It is a biological marker for assessing protein modifications from oxidative stress.^[1] In particular, it arises by iron-catalyzed reaction with hydrogen peroxide.^[2]

References

^ Uchida K, Kawakishi S (1993). "2-Oxo-histidine as a novel biological marker for oxidatively modified proteins". FEBS Lett. 332 (3): 208–210. Bibcode:1993FEBSL.332..208U. doi:10.1016/0014-5793(93)80632-5. PMID 8405458.
^ Lee, Jin-Won; Helmann, John D. (2006). "The PerR transcription factor senses H2O2 by metal-catalysed histidine oxidation". Nature. 440 (7082): 363–367. doi:10.1038/nature04537. PMID 16541078.