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Nitrotyrosine

Cayman Chemical Item Number 89540

(CAS 621-44-3)

Nitrotyrosine (CAS 621-44-3)

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Description

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 Physiol 271 C1424-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-Seyler 375 81-88 (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 Res 19 124-128 (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 Neurol 42 326-334 (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 Invest 94 2407-2413 (1994).

6 Ohya, M., Marukawa, S., Inoue, T., et al. Plasma nitrotyrosine concentration relates to prognosis in human septic shock. Shock 18(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 B 784 77-90 (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 Biochem 276 195-203 (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
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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 Physiol 271 C1424-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 Invest 94 2407-2413 (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 Biochem 276 195-203 (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 B 784 77-90 (2003).

Ohya, M., Marukawa, S., Inoue, T., et al. Plasma nitrotyrosine concentration relates to prognosis in human septic shock. Shock 18(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 Neurol 42 326-334 (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-Seyler 375 81-88 (1994).

Abe, K., Pan, L., Watanabe, M., et al. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis. Neurol Res 19 124-128 (1997).

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