2.02012-07-30 14:55:11 -06002015-06-03 17:21:04 -0600ECMDB21276M2MDB001683PhosphotyrosinePhosphotyrosine is a tyrosine (an amino acid) with a phosphate attached to its aromatic ring. Tyrosine (abbreviated as Tyr or Y) is one of the 22 amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. (Wikipedia) Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control. (PubChem) In E. coli, phosphotyrosine can act as a noncompetitive inhibitor of the enzyme biosynthetic ornithine decarboxylase. (EcoCyc)(S)-2-amino-3-(4-hydroxyphenyl)propanoate 4'-phosphate(S)-2-amino-3-(4-hydroxyphenyl)propanoic acid 4'-phosphate(S)-2-amino-3-(4-Hydroxyphenyl)propanoic acid 4'-phosphoric acidL-3-(4-Hydroxyphenyl)alanine 4'-phosphateL-3-(4-Hydroxyphenyl)alanine 4'-phosphoric acidL-PhosphotyrosineL-Tyrosine, dihydrogen phosphate (ester)L-Tyrosine, dihydrogen phosphoric acid (ester)L-Tyrosine-O-phosphateL-Tyrosine-O-phosphoric acidO-Phospho-L-tyrosineO-Phosphono-L-tyrosineO-PhosphotyrosineO4'-phospho-L-tyrosineO4-phosphono-L-tyrosineO4-phosphotyrosinePhospho-L-tyrosinePhosphonotyrosinePhosphotyrosinePhosphotyrosine (pY)Tyrosine O-phosphateTyrosine O-phosphoric acidTyrosine phosphateTyrosine phosphoric acidC9H12NO6P261.1684261.040223633(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acidphosphonotyrosine21820-51-9N[C@@H](CC1=CC=C(OP(O)(O)=O)C=C1)C(O)=OInChI=1S/C9H12NO6P/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H2,13,14,15)/t8-/m0/s1DCWXELXMIBXGTH-QMMMGPOBSA-NSolidExtra-organismPeriplasmlogp-0.76logs-2.13solubility1.93e+00 g/llogp-1.5pka_strongest_acidic1.38pka_strongest_basic9.46iupac(2S)-2-amino-3-[4-(phosphonooxy)phenyl]propanoic acidaverage_mass261.1684mono_mass261.040223633smilesN[C@@H](CC1=CC=C(OP(O)(O)=O)C=C1)C(O)=OformulaC9H12NO6PinchiInChI=1S/C9H12NO6P/c10-8(9(11)12)5-6-1-3-7(4-2-6)16-17(13,14)15/h1-4,8H,5,10H2,(H,11,12)(H2,13,14,15)/t8-/m0/s1inchikeyDCWXELXMIBXGTH-QMMMGPOBSA-Npolar_surface_area130.08refractivity57.97polarizability22.7rotatable_bond_count5acceptor_count6donor_count4physiological_charge-2formal_charge0tyrosine biosynthesisThe pathways of biosynthesis of phenylalaline and tyrosine are intimately connected. First step of both pathways is the conversion of chorismate to prephenate, the third step of both is the conversion of a ketoacid to the aminoacid through transamination. The two pathways differ only in the second step of their three-step reaction sequences: In the case of phenylalanine biosynthesi a dehydratase converts prephenate to phenylpyruvate(reaction occurs slowly in the absence of enzymic activity); in the case of tyrosine biosynthesis, a dehydrogenase converts prephenate to p-hydroxyphenylpyruvate. Also in both pathways the first two steps are catalyzed by two distinc active sites on a single protein. Thus the first step of each pathway can be catalyzed by two enzyme: those associated with both the phenylalanine specific dehydratase and the tyrosine specific dehydrogenase. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosinePW000806MetabolicSpecdb::CMs19420Specdb::CMs38949Specdb::CMs131361Specdb::CMs139095Specdb::NmrOneD61612Specdb::NmrOneD61613Specdb::NmrOneD61614Specdb::NmrOneD61615Specdb::NmrOneD61616Specdb::NmrOneD61617Specdb::NmrOneD61618Specdb::NmrOneD61619Specdb::NmrOneD61620Specdb::NmrOneD61621Specdb::NmrOneD61622Specdb::NmrOneD61623Specdb::NmrOneD61624Specdb::NmrOneD61625Specdb::NmrOneD61626Specdb::NmrOneD61627Specdb::NmrOneD61628Specdb::NmrOneD61629Specdb::NmrOneD61630Specdb::NmrOneD61631Specdb::MsMs23204Specdb::MsMs23205Specdb::MsMs23206Specdb::MsMs30002Specdb::MsMs30003Specdb::MsMs30004Specdb::MsMs2351341Specdb::MsMs2351342Specdb::MsMs2351343Specdb::MsMs2583956Specdb::MsMs2583957Specdb::MsMs2583958HMDB060493081928593C0650137788CPD-3728PTRPhosphotyrosineKataoka, H., Nakai, K., Katagiri, Y., Makita, M. (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection." Biomed Chromatogr 7:184-188.7693088Kataoka H, Nakai K, Makita M: Increase of phosphotyrosine levels in mouse urine and liver during liver regeneration after partial hepatectomy. Biochem Biophys Res Commun. 1994 Jun 15;201(2):909-16.7516161Munoz GE, Arenas-Diaz G, Marshall SH: Exogenously added free phosphotyrosine induces aggregation of circulating platelets in rabbits. Cell Mol Biol (Noisy-le-grand). 1992 Nov;38(7):719-22.1282059Periplasmic AppA proteinP07102PPA_ECOLIappAhttp://ecmdb.ca/proteins/P07102.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + Phosphotyrosine > Phosphate + L-Tyrosine