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Chem.: Phenyl pyruvic acid 2-oxo-3-phenyl-propanoic acid

Synonyms: 114-76-1, 156-06-9, 1PY, 2-Oxo-3-phenylpropanic acid, 2-Oxo-3-phenylpropanoic acid, 2-OXO-3-PHENYLPROPIONIC ACID, 3-phenyl-2-oxopropanoate, 3-Phenyl-2-oxopropanoic acid, 3-Phenylpyruvic acid, 51828-93-4, AIDS167235, AIDS-167235, alpha-ketohydrocinnamic acid, alpha-oxo-benzenepropanoic acid, Benzenepropanoic acid, .alpha.-oxo-, Benzenepropanoic acid, alpha-oxo-, beta-Phenylpyruvic acid, C00166, CHEBI:30851, EINECS 205-847-1, keto-phenylpyruvate, keto-phenylpyruvic acid, NSC1470, Phenylbrenztraubensaeure, phenylpyruvate, PHENYL-PYRUVATE, phenylpyruvic acid, PPY, Pyruvic acid, phenyl-

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Nakahara, T., Langenbeck, U., Zamora, R., Muskiet, F.A., Patel, M.S., et al.

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Disease relevance of Phenyl pyruvic acid

Untreated phenylketonuria (PKU) is characterized by excretion of phenylpyruvic acid in the urine and mental retardation [1].
Phenylalanine utilization for protein synthesis in beta-phenylpyruvic acid treated Escherichia coli cells [2].

High impact information on Phenyl pyruvic acid

Cobalt(II)-catalyzed chemiluminescence in a dioctadecyldimethylammonium chloride bilayer membranous medium for the flow injection determination of phenylpyruvic acid [3].
Identification and quantification of 3-methoxy-4-hydroxyphenyllactic acid (VLA) in cerebrospinal fluid and 3-methoxy-4-hydroxy phenylpyruvic acid (VPA) in the urine of Parkinsonian patients treated with L-DOPA [4].
In studies in vitro it was observed that the incorporation of the radioactivity from [14C]acetoacetate and 3-hydroxy[14C]butyrate into cerebral lipids was inhibited by phenyl-pyruvate, but not by phenylalanine [5].
The comparative formation of phenylalanine and phenylpyruvic acid in the reaction of 4,5-epoxy-2-decenal with phenylalanine was studied to determine whether epoyalkenals may also degrade amino acids without producing their decarboxylation [6].
Ferrichrome, rhodotorulic acid, desferoxamine mesylate and 2,3-dihydroxybenzoic acid were found to inhibit the MMP-2 activity whereas beta-phenylpyruvic acid had no effect [7].

Chemical compound and disease context of Phenyl pyruvic acid

There is a steady and nonlinear relationship between the levels of both phenylpyruvic acid (PPA) and o-hydroxyphenylacetic acid (oOPAA) in urine and the plasma levels of phenylalanine (phe) in children more than two years of age with phenylketonuria (PKU) [8].

Biological context of Phenyl pyruvic acid

As a possibility the defective decarboxylation of phenylpyruvic acid is proposed [9].
The use of engineered phenylalanine dehydrogenase N145A supported on Celite for the reductive amination of phenylpyruvic acid in homogeneous and biphasic aqueous-organic solvents is reported [10].

Associations of Phenyl pyruvic acid with other chemical compounds

The major catabolites detected by gas chromatography in the urines of infected animals were phenylpyruvic acid, 4-hydroxyphenylpyruvic acid, and indole-3-pyruvic acid [11].

Gene context of Phenyl pyruvic acid

[14C]-Benzylmalic acid was synthesized from beta-phenylpyruvic acid with [14C]-acetyl-CoA in the S10 fraction [12].

Analytical, diagnostic and therapeutic context of Phenyl pyruvic acid

Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection [13].
This sensitivity permits precise determination of several alpha-keto acids including phenylpyruvic acid, which cannot be determined by other HPLC methods, in 10 microliters of normal human plasma [13].

References

Eye findings in patients with phenylketonuria. Zwaan, J. Arch. Ophthalmol. (1983)
Phenylalanine utilization for protein synthesis in beta-phenylpyruvic acid treated Escherichia coli cells. Miseta, A., Csutora, P., Sipos, K., Wheatley, D.N. Microbios (1996)
Cobalt(II)-catalyzed chemiluminescence in a dioctadecyldimethylammonium chloride bilayer membranous medium for the flow injection determination of phenylpyruvic acid. Kishida, M., Makita, Y., Suzuki, T., Yamada, M., Hobo, T. Anal. Chem. (1991)
Identification and quantification of 3-methoxy-4-hydroxyphenyllactic acid (VLA) in cerebrospinal fluid and 3-methoxy-4-hydroxy phenylpyruvic acid (VPA) in the urine of Parkinsonian patients treated with L-DOPA. Muskiet, F.A., Jeuring, H.J., Teelken, A.W., Wolthers, B.G., Lakke, J.P. J. Neurochem. (1978)
Effect of hyperphenylalaninaemia on lipid synthesis from ketone bodies by rat brain. Patel, M.S., Owen, O.E. Biochem. J. (1976)
Chemical conversion of alpha-amino acids into alpha-keto acids by 4,5-epoxy-2-decenal. Zamora, R., Navarro, J.L., Gallardo, E., Hidalgo, F.J. J. Agric. Food Chem. (2006)
Effect of microbial siderophores on matrix metalloproteinase-2 activity. Gendron, R., Grenier, D., Sorsa, T., Uitto, V.J., Mayrand, D. J. Periodont. Res. (1999)
Absence of a significant renal threshold for two aromatic acids in phenylketonuric children over two years of age. Langenbeck, U., Behbehani, A., Mench-Hoinowski, A., Petersen, M. Eur. J. Pediatr. (1980)
Permanent chemical phenylketonuria and a normal phenylalanine tolerance in two sisters with a normal mental development. Wadman, S.K., Ketting, D., De Bree, P.K., Van der Heiden, C., Grimberg, M.T., Kruijswijk, H. Clin. Chim. Acta (1975)
Engineered phenylalanine dehydrogenase in organic solvents: homogeneous and biphasic enzymatic reactions. Cainelli, G., Engel, P.C., Galletti, P., Giacomini, D., Gualandi, A., Paradisi, F. Org. Biomol. Chem. (2005)
Increased excretion of aromatic amino acid catabolites in animals infected with Trypanosoma brucei evansi. El Sawalhy, A., Seed, J.R., Hall, J.E., El Attar, H. J. Parasitol. (1998)
Cell-free biosynthesis of arphamenine A. Okuyama, A., Ohuchi, S., Tanaka, T., Aoyagi, T., Umezawa, H. Biochem. Int. (1986)
Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Nakahara, T., Ishida, J., Yamaguchi, M., Nakamura, M. Anal. Biochem. (1990)