2.0 2012-05-31 10:23:39 -0600 2015-09-13 12:56:06 -0600 ECMDB00205 M2MDB000084 Phenylpyruvic acid Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Phenylalanine is converted to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. &alpha;-ketohydrocinnamate &alpha;-ketohydrocinnamic acid 2-Keto-phenyl-pyruvate 2-Keto-phenyl-pyruvic acid 2-Oxo-3-phenylpropanoate 2-Oxo-3-phenylpropanoic acid 3-Phenyl-2-oxopropanoate 3-Phenyl-2-oxopropanoic acid 3-Phenylpyruvate 3-Phenylpyruvic acid a-Ketohydrocinnamate a-Ketohydrocinnamic acid Alpha-Ketohydrocinnamate Alpha-Ketohydrocinnamic acid B-Phenylpyruvate B-Phenylpyruvic acid Beta-Phenylpyruvate Beta-Phenylpyruvic acid Keto-Phenylpyruvate Keto-Phenylpyruvic acid Phenylpyroracemate Phenylpyroracemic acid Phenylpyruvate α-Ketohydrocinnamate α-Ketohydrocinnamic acid β-Phenylpyruvate β-Phenylpyruvic acid C9H8O3 164.158 164.047344122 2-oxo-3-phenylpropanoic acid phenylpyruvic acid 156-06-9 OC(=O)C(=O)CC1=CC=CC=C1 InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) BTNMPGBKDVTSJY-UHFFFAOYSA-N Solid Cytosol melting_point 154 logp 1.9 ChemAxon pka_strongest_acidic 3.33 ChemAxon pka_strongest_basic -9.8 ChemAxon iupac 2-oxo-3-phenylpropanoic acid ChemAxon average_mass 164.158 ChemAxon mono_mass 164.047344122 ChemAxon smiles OC(=O)C(=O)CC1=CC=CC=C1 ChemAxon formula C9H8O3 ChemAxon inchi InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) ChemAxon inchikey BTNMPGBKDVTSJY-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 42.71 ChemAxon polarizability 15.75 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. 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 tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 phenylalanine biosynthesis The 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 biosynthesis, 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 tyrosine PW000807 Metabolic phenylalanine biosynthesis I PHESYN Specdb::CMs 458 Specdb::CMs 459 Specdb::CMs 460 Specdb::CMs 461 Specdb::CMs 462 Specdb::CMs 1216 Specdb::CMs 1278 Specdb::CMs 1383 Specdb::CMs 2776 Specdb::CMs 30240 Specdb::CMs 30915 Specdb::CMs 31068 Specdb::CMs 31069 Specdb::CMs 31070 Specdb::CMs 31618 Specdb::CMs 31619 Specdb::CMs 31620 Specdb::CMs 32188 Specdb::CMs 37354 Specdb::CMs 152691 Specdb::CMs 1054026 Specdb::CMs 1054028 Specdb::CMs 1054029 Specdb::EiMs 1076 Specdb::NmrOneD 1185 Specdb::NmrOneD 166333 Specdb::NmrOneD 166677 Specdb::MsMs 328 Specdb::MsMs 329 Specdb::MsMs 330 Specdb::MsMs 178839 Specdb::MsMs 178840 Specdb::MsMs 178841 Specdb::MsMs 181161 Specdb::MsMs 181162 Specdb::MsMs 181163 Specdb::MsMs 1471169 Specdb::MsMs 1471190 Specdb::MsMs 2234598 Specdb::MsMs 2327649 Specdb::MsMs 2327650 Specdb::MsMs 2327651 Specdb::MsMs 2634527 Specdb::MsMs 2634528 Specdb::MsMs 2634529 Specdb::NmrTwoD 1204 HMDB00205 997 972 C00166 18005 PHENYL-PYRUVATE PPY Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 5 pp. http://hmdb.ca/system/metabolites/msds/000/000/143/original/HMDB00205.pdf?1358462482 Aspartate aminotransferase P00509 AAT_ECOLI aspC http://ecmdb.ca/proteins/P00509.xml Aromatic-amino-acid aminotransferase P04693 TYRB_ECOLI tyrB http://ecmdb.ca/proteins/P04693.xml Histidinol-phosphate aminotransferase P06986 HIS8_ECOLI hisC http://ecmdb.ca/proteins/P06986.xml D-amino acid dehydrogenase small subunit P0A6J5 DADA_ECOLI dadA http://ecmdb.ca/proteins/P0A6J5.xml P-protein P0A9J8 PHEA_ECOLI pheA http://ecmdb.ca/proteins/P0A9J8.xml Branched-chain-amino-acid aminotransferase P0AB80 ILVE_ECOLI ilvE http://ecmdb.ca/proteins/P0AB80.xml alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid R00694 Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid R01373 PREPHENATEDEHYDRAT-RXN Prephenate <> Phenylpyruvic acid + Water + Carbon dioxide R01373 D-Phenylalanine + Water + Acceptor <> Phenylpyruvic acid + Ammonia + Reduced acceptor R01374 Phenylpyruvic acid + L-Glutamate <> L-Phenylalanine + Oxoglutaric acid PHEAMINOTRANS-RXN Prephenate > Phenylpyruvic acid + Water + Carbon dioxide Phenylpyruvic acid + Ammonia + cytochrome c nitrite reductase <> D-Phenylalanine + Water + cytochrome c nitrite reductase PW_R003457 Phenylpyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Phenylalanine + L-Phenylalanine PW_R002861 L-Phenylalanine + Oxygen + L-Phenylalanine <> Oxoglutaric acid + Phenylpyruvic acid PW_R003456 alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 89.8 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 359200 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 195.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 780000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 148.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 592000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621