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Chemical Compound Review

D-Tyrosin     (2R)-2-amino-3-(4- hydroxyphenyl)propanoic...

Synonyms: D-tyrosine, D-Tyr, D-TYR-OH, d-p-Tyrosine, H-D-Tyr-OH, ...
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Disease relevance of tyrosine

  • Patients with phenylketonuria (PKU) have a diet-controlled deficiency in the conversion of phenylalanine (Phe) to tyrosine (Tyr), leading to decreased production of noradrenaline, adrenaline, and dopamine [1].
  • The effect of obesity and tyrosine (tyr) supplements on catecholamine metabolism in 12 normal weight and nine obese adult women was studied [2].
  • To further elucidate the role of Stat3 in breast cancers, the expression patterns of Stat3 and Phospho-tyrosine residue 705 (Tyr705) Stat3 were correlated with survival outcome and clinicopathological parameters in a large cohort of node-negative breast cancer tumors [3].
  • The Phe/Cre ratios for five urines from patients with PKU ranged from 0.162 to 0.521, and the Tyr/Cre ratio for tyrosinemia was 0.147 [4].
  • The ratios of Tyr/Cre, Phe/Cre, and Trp/Cre for Lowe syndrome were 0.497, 0.321, and 0.495, respectively [4].

Psychiatry related information on tyrosine

  • We conclude that the route of administration is an important variable influencing the effects of Phe on feeding behavior, and that these effects are not readily explained by plasma or brain Phe and Tyr concentrations [5].
  • A few normal subjects had low TYR and TRP transport values, as observed in patients with affective disorders [6].
  • Overall reaction times of a central task were fastest after the BAL[1:1] meal concomitant to the highest overall tyrosine (Tyr) to LNAA ratio [7].

High impact information on tyrosine

  • Although cells transfected with c-fms genes containing either Tyr969 or Phe969 were not transformed, cotransfection of these genes with CSF-1 complementary DNA induced transformation, with c-fms(Phe969) showing significantly more activity than c-fms(Tyr969) [8].
  • Forty C-terminal amino acids of the normal receptor are replaced by 11 unrelated residues in the feline v-fms oncogene product, deleting a C-terminal tyrosine residue (Tyr969) whose phosphorylation might negatively regulate the receptor kinase activity [8].
  • Thr 14 and Tyr 15 are phosphorylated maximally during G2 phase but dephosphorylated abruptly at the G2/M transition, concomitant with activation of p34cdc2 kinase [9].
  • For neurochemistry, basal and K(+)-evoked release of the endogenous amino acids GABA, glutamate (Glu), aspartate (Asp), and tyrosine (Tyr) from micropunches of the CIC were measured in 8 age-paired animals from the 2 age groups using high-performance liquid chromatography [10].
  • In contrast, tissue content as well as basal and evoked release of Glu, Asp, Tyr, and 3H-ACh was similar between the 2 age groups [10].

Chemical compound and disease context of tyrosine

  • Therapeutic addition of Tyr to diets of mothers with even mild hyperphenylalaninaemia should be approached with caution as mild co-elevation of Phe and Tyr in the fetus may be harmful [11].
  • Three liver-specific growth media, respectively free of arginine (Arg-), tyrosine (Tyr-) and glucose (G-), have been used to characterize cells of the rat H4IIEC3, human HepG2 and mouse BW hepatoma lines [12].

Biological context of tyrosine

  • These results strongly suggest that like the STATs, the IRFs are also modulated by Tyr phosphorylation that affects their biological activities [13].
  • Substitution of Asn(726) with Phe or Tyr also produces self-poisoning enzymes, implicating stacking interactions in the increased kinetics of DNA cleavage by Top1N726Hp and Top1N726Fp [14].
  • The data indicate that decreased IR tyr phosphorylation in hyperglycemia-induced insulin resistance is not due to enhanced dephosphorylation [15].
  • Gyrase containing mutations in the A subunit at either the active-site tyrosine (Tyr122) or Ser83 (a residue known to be involved in quinolone interaction) failed to halt the progress of the polymerase [16].
  • We conclude that urinary catecholamine metabolite production is related to body composition and to tyr intake in normal weight women [2].

Anatomical context of tyrosine

  • To assess tyr dephosphorylation, IRs of insulin-stimulated permeabilized adipocytes were labeled with [gamma-32P]ATP and chased for 2 min with unlabeled ATP in the presence of EDTA [15].
  • Studying normal human keratinocytes (NHKs), here we demonstrate strong expression of the Src family kinases Src, Yes, and Fyn; Src family kinase-dependent stimulation of Tyr 845 by EGF; and potent inhibition of NHK proliferation and migration by two Src family kinase inhibitors PP1 and PD173952 [17].
  • Tyr/Phe restriction also inhibits Bcl-2 and Met restriction inhibits Bcl-XL in mitochondria [18].
  • Treatment of serum-starved astrocytes with thrombin resulted in a rapid activation of tyrosine (Tyr) phosphorylation of a set of proteins including a prominent one with a molecular mass of 42 kDa (p42) [19].
  • Restriction of Tyr/Phe or Met in DU145 and Met in PC3 reduces mitochondrial membrane potential (DeltaPsim) and induces caspase-dependent and -independent apoptosis [18].

Associations of tyrosine with other chemical compounds


Gene context of tyrosine


Analytical, diagnostic and therapeutic context of tyrosine

  • Kd for the drug-hcTnC interaction in the presence of Ca2+, determined by Tyr fluorescence titrations, was approximately 40 microM [20].
  • After treatment with Tyr, ganglionic transmission was depressed significantly (p less than 0.05) in response to both low- and high-frequency stimulation (single: 0.44 +/- 0.04 mV; low: 0.22 +/- 0.12 mV; high: 0.26 +/- 0.07 mV) [30].
  • PEG 8000 perturbs the structure of the protein surface, partially modifying the layer of water and the microenvironment of the superficial aromatic residues (tryptophan, TRP and TYR) which is in agreement with the modifications of the UV spectrum of albumin by PEG 8000 and circular dichroism (CD) spectrum at high temperatures [31].


  1. Morning preprandial plasma ghrelin and catecholamine concentrations in patients with phenylketonuria and normal controls: evidence for catecholamine-mediated ghrelin regulation. Schulpis, K.H., Papassotiriou, I., Vounatsou, M., Karikas, G.A., Tsakiris, S., Chrousos, G.P. J. Clin. Endocrinol. Metab. (2004) [Pubmed]
  2. Obesity and precursor availability affect urinary catecholamine metabolite production in women. Johnston, J.L., Warsh, J.J., Anderson, G.H. Am. J. Clin. Nutr. (1983) [Pubmed]
  3. Tissue microarray analysis of signal transducers and activators of transcription 3 (Stat3) and phospho-Stat3 (Tyr705) in node-negative breast cancer shows nuclear localization is associated with a better prognosis. Dolled-Filhart, M., Camp, R.L., Kowalski, D.P., Smith, B.L., Rimm, D.L. Clin. Cancer Res. (2003) [Pubmed]
  4. Simultaneous determination of creatinine, creatine, and UV-absorbing amino acids using dual-mode gradient low-capacity cation-exchange chromatography. Yokoyama, Y., Tsuji, S., Sato, H. Journal of chromatography. A. (2005) [Pubmed]
  5. Route of delivery of phenylalanine influences its effect on short-term food intake in adult male rats. Bialik, R.J., Li, E.T., Geoffroy, P., Anderson, G.H. J. Nutr. (1989) [Pubmed]
  6. Individuality and stability in the transport of precursors of monoamines across the erythrocyte membrane of mentally normal subjects. Schulz, P., Bugman, I.T., Widmer, J., Dick, P., Tissot, R. Neuropsychobiology (1988) [Pubmed]
  7. Carbohydrate to protein ratio in food and cognitive performance in the morning. Fischer, K., Colombani, P.C., Langhans, W., Wenk, C. Physiol. Behav. (2002) [Pubmed]
  8. Transforming potential of the c-fms proto-oncogene (CSF-1 receptor). Roussel, M.F., Dull, T.J., Rettenmier, C.W., Ralph, P., Ullrich, A., Sherr, C.J. Nature (1987) [Pubmed]
  9. Differential phosphorylation of vertebrate p34cdc2 kinase at the G1/S and G2/M transitions of the cell cycle: identification of major phosphorylation sites. Krek, W., Nigg, E.A. EMBO J. (1991) [Pubmed]
  10. Immunocytochemical and neurochemical evidence for age-related loss of GABA in the inferior colliculus: implications for neural presbycusis. Caspary, D.M., Raza, A., Lawhorn Armour, B.A., Pippin, J., Arnerić, S.P. J. Neurosci. (1990) [Pubmed]
  11. Outcome of pregnancy in the rat with mild hyperphenylalaninaemia and hypertyrosinaemia: implications for the management of "human maternal PKU". Lewis, S.A., Lyon, I.C., Elliott, R.B. J. Inherit. Metab. Dis. (1985) [Pubmed]
  12. Selection of variant hepatoma cells in liver-specific growth media: regulation at the mRNA level. Armbruster, L., Cavard, C., Briand, P., Bertolotti, R. Differentiation (1992) [Pubmed]
  13. Phosphorylation events modulate the ability of interferon consensus sequence binding protein to interact with interferon regulatory factors and to bind DNA. Sharf, R., Meraro, D., Azriel, A., Thornton, A.M., Ozato, K., Petricoin, E.F., Larner, A.C., Schaper, F., Hauser, H., Levi, B.Z. J. Biol. Chem. (1997) [Pubmed]
  14. Substitution of conserved residues within the active site alters the cleavage religation equilibrium of DNA topoisomerase I. Colley, W.C., van der Merwe, M., Vance, J.R., Burgin, A.B., Bjornsti, M.A. J. Biol. Chem. (2004) [Pubmed]
  15. Decreased in situ insulin receptor dephosphorylation in hyperglycemia-induced insulin resistance in rat adipocytes. Tang, S., Le-Tien, H., Goldstein, B.J., Shin, P., Lai, R., Fantus, I.G. Diabetes (2001) [Pubmed]
  16. The complex of DNA gyrase and quinolone drugs on DNA forms a barrier to the T7 DNA polymerase replication complex. Wentzell, L.M., Maxwell, A. J. Mol. Biol. (2000) [Pubmed]
  17. Src family kinase inhibitors block amphiregulin-mediated autocrine ErbB signaling in normal human keratinocytes. Kansra, S., Stoll, S.W., Johnson, J.L., Elder, J.T. Mol. Pharmacol. (2005) [Pubmed]
  18. Selective amino acid restriction targets mitochondria to induce apoptosis of androgen-independent prostate cancer cells. Fu, Y.M., Zhang, H., Ding, M., Li, Y.Q., Fu, X., Yu, Z.X., Meadows, G.G. J. Cell. Physiol. (2006) [Pubmed]
  19. Thrombin activates mitogen-activated protein kinase in primary astrocyte cultures. Bhat, N.R., Zhang, P., Hogan, E.L. J. Cell. Physiol. (1995) [Pubmed]
  20. Interaction of cardiotonic thiadiazinone derivatives with cardiac troponin C. Pan, B.S., Johnson, R.G. J. Biol. Chem. (1996) [Pubmed]
  21. Phenylethylaminergic mechanisms in attention-deficit disorder. Baker, G.B., Bornstein, R.A., Rouget, A.C., Ashton, S.E., van Muyden, J.C., Coutts, R.T. Biol. Psychiatry (1991) [Pubmed]
  22. Cerebrospinal fluid monoamine precursor and metabolite levels in children treated for leukemia: age and sex effects and individual variability. Riddle, M.A., Anderson, G.M., McIntosh, S., Harcherik, D.F., Shaywitz, B.A., Cohen, D.J. Biol. Psychiatry (1986) [Pubmed]
  23. The effects of a branched chain amino acid mixture supplemented with tryptophan on biochemical indices of neurotransmitter function and decision-making. Scarnà, A., McTavish, S.F., Cowen, P.J., Goodwin, G.M., Rogers, R.D. Psychopharmacology (Berl.) (2005) [Pubmed]
  24. Activation of D-tyrosine by Bacillus stearothermophilus tyrosyl-tRNA synthetase: 2. Cooperative binding of ATP is limited to the initial turnover of the enzyme. Sheoran, A., First, E.A. J. Biol. Chem. (2008) [Pubmed]
  25. Activation of D-tyrosine by Bacillus stearothermophilus tyrosyl-tRNA synthetase: 1. Pre-steady-state kinetic analysis reveals the mechanistic basis for the recognition of D-tyrosine. Sheoran, A., Sharma, G., First, E.A. J. Biol. Chem. (2008) [Pubmed]
  26. Protein phosphatase 2A activity associated with Golgi membranes during the G2/M phase may regulate phosphorylation of ERK2. Hancock, C.N., Dangi, S., Shapiro, P. J. Biol. Chem. (2005) [Pubmed]
  27. Cytotoxic T lymphocyte-associated molecule-4, a high-avidity receptor for CD80 and CD86, contains an intracellular localization motif in its cytoplasmic tail. Leung, H.T., Bradshaw, J., Cleaveland, J.S., Linsley, P.S. J. Biol. Chem. (1995) [Pubmed]
  28. Role of protein phosphatase 2A in mGluR5-regulated MEK/ERK phosphorylation in neurons. Mao, L., Yang, L., Arora, A., Choe, E.S., Zhang, G., Liu, Z., Fibuch, E.E., Wang, J.Q. J. Biol. Chem. (2005) [Pubmed]
  29. Cyclin A/Cdk2 complexes regulate activation of Cdk1 and Cdc25 phosphatases in human cells. Mitra, J., Enders, G.H. Oncogene (2004) [Pubmed]
  30. Effect of precursors on the synthesis of catecholamines and on neurotransmission in the superior cervical ganglion of the rat. Zhang, C., Bordet, S., Karoum, F., Commissiong, J.W. J. Neurochem. (1990) [Pubmed]
  31. Thermal features of the bovine serum albumin unfolding by polyethylene glycols. Farruggia, B., Nerli, B., Di Nuci, H., Rigatusso, R., Picó, G. Int. J. Biol. Macromol. (1999) [Pubmed]
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