2.0 2012-08-09 09:25:15 -0600 2015-06-03 17:21:42 -0600 ECMDB21520 M2MDB001915 D-Tyrosine D-Tyrosine is one of the two enantiomers of tyrosine. Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 22 amino acids that are used by cells to synthesize proteins. Its codons are UAC and UAU. It is a non-essential amino acid with a polar side group. (Wikipedia) L-Tyrosine is the correct tyrosine isomer used in building proteins, and aminoacyl-tRNA synthetases ensure the exclusion of D-amino acids like D-tyrosine from translation. But sometimes, tyrosyl-tRNA synthetases use D-tyrosine by mistake. Hence, D-tyrosine can be toxic to E. coli, especially in absence of D-Tyr-tRNATyr deacylase to remove the incorrectly-made tRNAs containing D-tyrosine. (PMID 15292242) (-)-a-Amino-p-hydroxyhydrocinnamate (-)-a-Amino-p-hydroxyhydrocinnamic acid (-)-alpha-Amino-p-hydroxyhydrocinnamate (-)-alpha-Amino-p-hydroxyhydrocinnamic acid (-)-α-amino-P-Hydroxyhydrocinnamate (-)-α-amino-P-Hydroxyhydrocinnamic acid (2R)-2-amino-3-(4-hydroxyphenyl)propanoate (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid (R)-2-Amino-3-(p-hydroxyphenyl)propionate (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid (R)-3-(p-Hydroxyphenyl)alanine (S)-(-)-Tyrosine (S)-2-Amino-3-(p-hydroxyphenyl)propionate (S)-2-amino-3-(p-hydroxyphenyl)propionic acid (S)-3-(p-hydroxyphenyl)alanine (S)-a-amino-4-hydroxy-Benzenepropanoate (S)-a-amino-4-hydroxy-Benzenepropanoic acid (S)-a-Amino-4-hydroxybenzenepropanoate (S)-a-Amino-4-hydroxybenzenepropanoic acid (S)-alpha-amino-4-hydroxy-Benzenepropanoate (S)-alpha-amino-4-hydroxy-Benzenepropanoic acid (S)-alpha-Amino-4-hydroxybenzenepropanoate (S)-alpha-Amino-4-hydroxybenzenepropanoic acid (S)-Tyrosine (S)-α-amino-4-Hydroxy-benzenepropanoate (S)-α-amino-4-Hydroxy-benzenepropanoic acid (S)-α-amino-4-Hydroxybenzenepropanoate (S)-α-amino-4-Hydroxybenzenepropanoic acid 2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoate 2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-Propanoic acid 2-amino-3-(4-Hydroxyphenyl)-propanoate 2-amino-3-(4-hydroxyphenyl)-propanoic acid 3-(4-Hydroxyphenyl)-L-alanine 4-Hydroxy-L-Phenylalanine Benzenepropanoate Benzenepropanoic acid D-Tyr D-Tyrosin D-Tyrosine L-p-Tyrosine L-Tyrosine P-Tyrosine Tyr Tyrosine C9H11NO3 181.1885 181.073893223 (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid (.+-.)-tyrosine 556-02-5 N[C@H](CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1 OUYCCCASQSFEME-MRVPVSSYSA-N Solid logp -2.39 ALOGPS logs -1.37 ALOGPS solubility 7.67e+00 g/l ALOGPS melting_point 343 oC logp -1.5 ChemAxon pka_strongest_acidic 2 ChemAxon pka_strongest_basic 9.19 ChemAxon iupac (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid ChemAxon average_mass 181.1885 ChemAxon mono_mass 181.073893223 ChemAxon smiles N[C@H](CC1=CC=C(O)C=C1)C(O)=O ChemAxon formula C9H11NO3 ChemAxon inchi InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1 ChemAxon inchikey OUYCCCASQSFEME-MRVPVSSYSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 47.1 ChemAxon polarizability 18.06 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2899 Specdb::NmrOneD 4619 Specdb::NmrOneD 256108 Specdb::NmrOneD 256109 Specdb::NmrOneD 256110 Specdb::NmrOneD 256111 Specdb::NmrOneD 256112 Specdb::NmrOneD 256113 Specdb::NmrOneD 256114 Specdb::NmrOneD 256115 Specdb::NmrOneD 256116 Specdb::NmrOneD 256117 Specdb::NmrOneD 256118 Specdb::NmrOneD 256119 Specdb::NmrOneD 256120 Specdb::NmrOneD 256121 Specdb::NmrOneD 256122 Specdb::NmrOneD 256123 Specdb::NmrOneD 256124 Specdb::NmrOneD 256125 Specdb::NmrOneD 256126 Specdb::NmrOneD 256127 Specdb::MsMs 29459 Specdb::MsMs 29460 Specdb::MsMs 29461 Specdb::MsMs 36017 Specdb::MsMs 36018 Specdb::MsMs 36019 HMDB00158 71098 5833 C06420 28479 D-TYROSINE DTY Tyrosine Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Soutourina, O., Soutourina, J., Blanquet, S., Plateau, P. (2004). "Formation of D-tyrosyl-tRNATyr accounts for the toxicity of D-tyrosine toward Escherichia coli." J Biol Chem 279:42560-42565. 15292242