Nitrotyrosine is formed by peroxynitrite-mediated nitration of protein tyrosine residues. Its presence on proteins can be used as a marker for peroxynitrite formation in vivo.1,2,3,4 Both free and protein-bound nitrotyrosine are commonly found in mammalian tissues and are increased in pathological conditions.2,5,6 The basal levels of free nitrotyrosine in human plasma is approximately 3 nM as determined by GC/MS.7,8
1
Beckman, J.S., and Koppenol, W.H. Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and the ugly. Am J Physiol271C1424-C1437(1996).
2
Beckman, J.S., Ye, Y.Z., Anderson, P.G., et al. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol Chem Hoppe-Seyler37581-88(1994).
3
Abe, K., Pan, L., Watanabe, M., et al. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis. Neurol Res19124-128(1997).
4
Ferrante, R.J., Shinobu, L.A., Schulz, J.B., et al. Increased 3-nitrotyrosine and oxidative damage in mice with a human copper/zinc superoxide dismutase mutation. Ann Neurol42326-334(1997).
5
Haddad, I.Y., Pataki, G., Hu, P., et al. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J Clin Invest942407-2413(1994).
6
Ohya, M., Marukawa, S., Inoue, T., et al. Plasma nitrotyrosine concentration relates to prognosis in human septic shock. Shock18(2)116-118(2002).
7
Tsikas, D., Schwedhelm, E., Stutzer, F.K., et al. Accurate quantification of basal plasma levels of 3-nitrotyrosine and 3-nitrotyrosinoalbumin by gas chromatography-tandem mass spectrometry. J Chromatogr B78477-90(2003).
8
Schwedhelm, E., Tsikas, D., Gutzki, F., et al. Gas chromatographic-tandem mass spectrometric quantification of free 3-nitrotyrosine in human plasma at the basal state. Anal Biochem276195-203(1999).
Formal Name
3-nitro-L-tyrosine
CAS Number
621-44-3
Molecular Formula
C9H10N2O5
Formula Weight
226.2
Formulation
A crystalline solid
Purity
>99%
λmax
217, 274, 355 nm
Stability
2 years
Storage
Room temperature
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
OC(=O)[C@@H](N)Cc1ccc(O)c(c1)[N](=O)O
Background Reading
Beckman, J.S., and Koppenol, W.H. Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and the ugly. Am J Physiol271C1424-C1437(1996).
Haddad, I.Y., Pataki, G., Hu, P., et al. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J Clin Invest942407-2413(1994).
Schwedhelm, E., Tsikas, D., Gutzki, F., et al. Gas chromatographic-tandem mass spectrometric quantification of free 3-nitrotyrosine in human plasma at the basal state. Anal Biochem276195-203(1999).
Tsikas, D., Schwedhelm, E., Stutzer, F.K., et al. Accurate quantification of basal plasma levels of 3-nitrotyrosine and 3-nitrotyrosinoalbumin by gas chromatography-tandem mass spectrometry. J Chromatogr B78477-90(2003).
Ohya, M., Marukawa, S., Inoue, T., et al. Plasma nitrotyrosine concentration relates to prognosis in human septic shock. Shock18(2)116-118(2002).
Ferrante, R.J., Shinobu, L.A., Schulz, J.B., et al. Increased 3-nitrotyrosine and oxidative damage in mice with a human copper/zinc superoxide dismutase mutation. Ann Neurol42326-334(1997).
Beckman, J.S., Ye, Y.Z., Anderson, P.G., et al. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol Chem Hoppe-Seyler37581-88(1994).
Abe, K., Pan, L., Watanabe, M., et al. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis. Neurol Res19124-128(1997).