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Chemical Compound Review

O-Tyrosine     2-amino-3-(2- hydroxyphenyl)propanoic acid

Synonyms: Ortho-tyrosine, DL-o-Tyrosine, o-DL-Tyrosine, H-DL-O-TYR-OH, D,L-o-Tyrosine, ...
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Disease relevance of NSC 72345


High impact information on NSC 72345

  • Moreover, hepatic levels of protein-bound dityrosine and ortho-tyrosine, two markers of metal-catalyzed oxidative damage in vitro, failed to rise in iron-overloaded animals [5].
  • In contrast, MPTP failed to alter levels of ortho-tyrosine in any brain region we studied [6].
  • Exercise led to a 50% increase in ortho-tyrosine, metatyrosine, and o,o'-dityrosine in the mitochondrial proteins but not cytosolic proteins of heart muscle [7].
  • Ortho-tyrosine showed an inverse relationship with forced vital capacity (p = .01) but was not related to inflammation of the upper airways as assessed by cell counts of polymorphonuclear neutrophils [8].
  • The aim of this study was to measure para- and ortho-tyrosine in the urine and plasma of patients with chronic renal disease and/or diabetes, to obtain information on the renal handling of the different tyrosine isomers and, furthermore, to measure urinary levels of 8-epi-prostaglandin-F(2alpha), a marker of lipid peroxidation [2].

Biological context of NSC 72345

  • HPLC measurements of the effluent were performed using photodiode array detection for determination of phenylalanine derived o-tyrosine and m-tyrosine (as hydroxylation markers) as well as of nitrotyrosine and nitrophenylalanine (as nitration markers) [9].
  • AMPA receptor functional tests showed that the o-tyrosine analogues are antagonists and that the S-isomer 6b (IC50 = 630 +/- 140 microM) was more potent than the racemate 6 (IC50 = 730 +/- 88 microM) while the R-isomer 6a was inactive up to 1 mM concentration, which is consistent with the S-isomer having higher binding affinity than the R-isomer [10].
  • To test the hypothesis that kwashiorkor is associated with increased oxidative stress, urinary concentrations of 2 oxidized amino acids, o,o '-dityrosine and ortho -tyrosine, were measured by gas chromatography-mass spectrometry [3].
  • Low-temperature measurements have detected a very rapid initial anisotropy decay in the 2-tyrosine species which may be attributed to radiationless energy transfer between the two tyrosines [11].
  • The procedure involves the solvent extraction and removal of free o-tyrosine, which is present in unirradiated tissue, followed by acid hydrolysis of bound o-tyrosine in the proteinaceous residue and measurement of the cleaved residues by HPLC with fluorescence detection [12].

Anatomical context of NSC 72345

  • Caloric restriction prevented the increase in o,o'-dityrosine levels in cardiac and skeletal muscle but did not influence o-tyrosine levels in any of the four tissues [13].
  • To determine whether HO. is formed in the oral cavity during AQ chewing, the formation of meta-tyrosine (m-Tyr) and ortho-tyrosine (o-Tyr) from l-phenylalanine (Phe) was confirmed [14].
  • The analysis of pA2 values for 1,2-substituted oxytocin analogues suggests a significant resonance effect of p-substituted groups in 2-tyrosine when the hormone binds to its uterus receptor, whereas the N-terminal amino group exerts less clearly characterized effects (participation of its lipophilicity and molecular volume can be assumed [15].

Associations of NSC 72345 with other chemical compounds


Gene context of NSC 72345


Analytical, diagnostic and therapeutic context of NSC 72345

  • Quantification of o-tyrosine, o-nitrotyrosine, and o,o'dityrosine from cat urine samples was achieved by LC/ electrospray ionization-MS/MS (LC/ESI-MS/MS) using an isotope dilution technique in multiple reaction monitoring mode before butylation of o,o'-dityrosine and after butylation of o-tyrosine and o-nitrotyrosine [23].
  • Determination of m-tyrosine and o-tyrosine in human serum by high-performance liquid chromatography with fluorimetric detection [24].
  • Oxidant injury was assessed before and after treatment by plasma and urine levels of malondialdehyde (MDA) and o-tyrosine [20].
  • After 5 min of ischemia, net cumulative rates of production of p-, m-, and o-tyrosine during reperfusion were 177 +/- 63, 74 +/- 26, and 1.6 +/- 0.8 nmol.min-1.g-1, respectively, whereas after 10 min of ischemia production rates were 153 +/- 42, 78 +/- 29, and 2.1 +/- 0.5 nmol.min-1.g-1, respectively [4].


  1. Reactive carbonyls and polyunsaturated fatty acids produce a hydroxyl radical-like species: a potential pathway for oxidative damage of retinal proteins in diabetes. Pennathur, S., Ido, Y., Heller, J.I., Byun, J., Danda, R., Pergola, P., Williamson, J.R., Heinecke, J.W. J. Biol. Chem. (2005) [Pubmed]
  2. Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Molnár, G.A., Wagner, Z., Markó, L., Kó Szegi, T., Mohás, M., Kocsis, B., Matus, Z., Wagner, L., Tamaskó, M., Mazák, I., Laczy, B., Nagy, J., Wittmann, I. Kidney Int. (2005) [Pubmed]
  3. Increased oxidative stress in kwashiorkor. Manary, M.J., Leeuwenburgh, C., Heinecke, J.W. J. Pediatr. (2000) [Pubmed]
  4. Hydroxyl radical production during myocardial ischemia and reperfusion in cats. O'Neill, C.A., Fu, L.W., Halliwell, B., Longhurst, J.C. Am. J. Physiol. (1996) [Pubmed]
  5. Iron overload diminishes atherosclerosis in apoE-deficient mice. Kirk, E.A., Heinecke, J.W., LeBoeuf, R.C. J. Clin. Invest. (2001) [Pubmed]
  6. Mass spectrometric quantification of 3-nitrotyrosine, ortho-tyrosine, and o,o'-dityrosine in brain tissue of 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyridine-treated mice, a model of oxidative stress in Parkinson's disease. Pennathur, S., Jackson-Lewis, V., Przedborski, S., Heinecke, J.W. J. Biol. Chem. (1999) [Pubmed]
  7. Hydroxyl radical generation during exercise increases mitochondrial protein oxidation and levels of urinary dityrosine. Leeuwenburgh, C., Hansen, P.A., Holloszy, J.O., Heinecke, J.W. Free Radic. Biol. Med. (1999) [Pubmed]
  8. Aromatic hydroxylation in nasal lavage fluid following ambient ozone exposure. Frischer, T., Pullwitt, A., Kühr, J., Meinert, R., Haschke, N., Studnicka, M., Lubec, G. Free Radic. Biol. Med. (1997) [Pubmed]
  9. 6-hydroxydopamine increases the hydroxylation and nitration of phenylalanine in vivo: implication of peroxynitrite formation. Ferger, B., Themann, C., Rose, S., Halliwell, B., Jenner, P. J. Neurochem. (2001) [Pubmed]
  10. Design and synthesis of enantiomers of 3,5-dinitro-o-tyrosine: alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonists. Sun, G., Slavica, M., Uretsky, N.J., Wallace, L.J., Shams, G., Weinstein, D.M., Miller, J.C., Miller, D.D. J. Med. Chem. (1998) [Pubmed]
  11. Intensity and anisotropy decays of the tyrosine calmodulin proteolytic fragments, as studied by GHz frequency-domain fluorescence. Gryczynski, I., Steiner, R.F., Lakowicz, J.R. Biophys. Chem. (1991) [Pubmed]
  12. Detection of o-tyrosine in irradiated chicken by reverse-phase HPLC and fluorescence detection. Ibe, F.I., Grinter, R., Massey, R., Homer, R. Food additives and contaminants. (1991) [Pubmed]
  13. Caloric restriction attenuates dityrosine cross-linking of cardiac and skeletal muscle proteins in aging mice. Leeuwenburgh, C., Wagner, P., Holloszy, J.O., Sohal, R.S., Heinecke, J.W. Arch. Biochem. Biophys. (1997) [Pubmed]
  14. Ingredients contribute to variation in production of reactive oxygen species by areca quid. Chen, P.H., Tsai, C.C., Lin, Y.C., Ko, Y.C., Yang, Y.H., Shieh, T.Y., Ho, P.S., Li, C.M., Min-Shan Ko, A., Chen, C.H. J. Toxicol. Environ. Health Part A (2006) [Pubmed]
  15. Affinity of 1,2-substituted oxytocin analogues to the uterus receptor: Free-Wilson and Hansch analysis. Pliska, V. Experientia (1978) [Pubmed]
  16. Hyperoxic injury of immature guinea pig lung is mediated via hydroxyl radicals. Kelly, F.J., Lubec, G. Pediatr. Res. (1995) [Pubmed]
  17. Comparative time-courses of copper-ion-mediated protein and lipid oxidation in low-density lipoprotein. Knott, H.M., Baoutina, A., Davies, M.J., Dean, R.T. Arch. Biochem. Biophys. (2002) [Pubmed]
  18. Evidence against the involvement of reactive oxygen species in the pathogenesis of neuronal death in Down's syndrome and Alzheimer's disease. Hayn, M., Kremser, K., Singewald, N., Cairns, N., Nemethova, M., Lubec, B., Lubec, G. Life Sci. (1996) [Pubmed]
  19. The hydroxyl radical formation system in polymorphonuclear leukocytes. Kawakami, N., Hayakawa, T., Shimohama, S., Fujimoto, S. Biol. Pharm. Bull. (1999) [Pubmed]
  20. Effect of intravenous iron supplementation on erythropoiesis in erythropoietin-treated premature infants. Pollak, A., Hayde, M., Hayn, M., Herkner, K., Lombard, K.A., Lubec, G., Weninger, M., Widness, J.A. Pediatrics (2001) [Pubmed]
  21. Decrease of brain protein kinase C, protein kinase A, and cyclin-dependent kinase correlating with pH precedes neuronal death in neonatal asphyxia. Lubec, B., Dell'Anna, E., Fang-Kircher, S., Marx, M., Herrera-Marschitz, M., Lubec, G. J. Investig. Med. (1997) [Pubmed]
  22. Oxyradical damage and mitochondrial enzyme activities in the mdx mouse. Hauser, E., Höger, H., Bittner, R., Widhalm, K., Herkner, K., Lubec, G. Neuropediatrics. (1995) [Pubmed]
  23. Quantification of o,o'-dityrosine, o-nitrotyrosine, and o-tyrosine in cat urine samples by LC/ electrospray ionization-MS/MS using isotope dilution. Marvin, L.F., Delatour, T., Tavazzi, I., Fay, L.B., Cupp, C., Guy, P.A. Anal. Chem. (2003) [Pubmed]
  24. Determination of m-tyrosine and o-tyrosine in human serum by high-performance liquid chromatography with fluorimetric detection. Ishimitsu, S., Fujimoto, S., Ohara, A. J. Chromatogr. (1986) [Pubmed]
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