Nitrotyrosine
- (2S)- 2-amino- 3-( 4-hydroxy- 3-nitrophenyl ) propanoic acid (IUPAC)
- L-( -)- nitrotyrosine
- ( S) - ( -)- nitrotyrosine
- D-( )- nitrotyrosine
- ( R) - ( )- nitrotyrosine
- 3-nitro -L- tyrosine
Yellow- greenish solid
233-235 ° C ( decomposition)
Insoluble in water
Template: Infobox chemical / molecular formula search available
Nitrotyrosine, correct 3- nitrotyrosine, is a non- proteinogenic amino acid. The compound is formed in organisms by the action of reactive nitrogen species peroxynitrite on tyrosine.
Properties
3- nitrotyrosine is a derivative of the proteinogenic amino acid tyrosine. It is a yellowish to slightly greenish solid having a decomposition point at about 235 ° C.
Occurrence and formation
Of the two possible enantiomers of chiral 3- Nitrotyrosins comes in organisms from only the L-form. There it is formed from the proteinogenic amino acid tyrosine by the action of peroxynitrite anion ( nucleophilic aromatic substitution).
Biomarkers
3-nitro -L- tyrosine is used in laboratory diagnostics as a biomarker of nitrosative stress. In a number of diseases, such as gastric cancer, atherosclerosis, pulmonary diseases ( such as asthma), sepsis, vasculitis, and other inflammatory diseases the level of 3-nitro- L-tyrosine is increased in the blood serum. Generally, the compound is a biomarker for apoptosis (programmed cell death).
The detection of 3-nitro -L- tyrosine, for example, via HPLC -MS.