1.13.11.27 (2-fluoro-4-hydroxyphenyl)pyruvate + O2 - Pseudomonas sp. (3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2 - ? 260712 1.13.11.27 (2-fluoro-4-hydroxyphenyl)pyruvate + O2 - Pseudomonas sp. P.J. 874 (3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2 - ? 260712 1.13.11.27 (4-hydroxyphenyl)-pyruvate + O2 - Streptomyces avermitilis homogentisate + CO2 - ? 375441 1.13.11.27 2-thienylpyruvate + O2 - Sus scrofa ? + CO2 - ? 260715 1.13.11.27 3,4-dihydroxyphenylpyruvate + O2 - Gallus gallus ? + CO2 - ? 260709 1.13.11.27 3,4-dihydroxyphenylpyruvate + O2 - Rattus norvegicus ? + CO2 - ? 260709 1.13.11.27 3-thienylpyruvate + O2 - Sus scrofa 3-carboxymethyl-3-thiolene-2-one + CO2 - ? 260716 1.13.11.27 4-fluorophenylpyruvate + O2 - Gallus gallus 4-fluoro-2-hydroxyphenylacetate + CO2 - ? 260711 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Gallus gallus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Synechococcus elongatus PCC 7942 = FACHB-805 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Cavia porcellus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Homo sapiens homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Rattus norvegicus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Sus scrofa homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Bos taurus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Oryctolagus cuniculus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Zea mays homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Arabidopsis thaliana homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Avena sativa homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Pseudomonas fluorescens homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Pseudomonas sp. homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Canis lupus familiaris homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Arabidopsis sp. homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Frog homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Platyrrhini homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Daucus carota homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Streptomyces coelicolor homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Echinochloa crus-galli homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Enterobacter sp. homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Ralstonia pickettii homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Oncorhynchus mykiss homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Didelphidae homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Streptomyces avermitilis homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Setaria faberi homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Paracoccidioides brasiliensis homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Salvia miltiorrhiza homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Coptis japonica var. dissecta homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Shewanella oneidensis homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Picrophilus torridus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Medicago sativa homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Sphingobium sp. homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Klebsiella pneumoniae homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Alcaligenes faecalis homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Shewanella oneidensis homogentisate + CO2 homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 best substrate Sus scrofa homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 activity with the keto-form of 4-hydroxyphenylpyruvate is 40times higher than with the enol tautomer Homo sapiens homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 evidence against participation of a quinol as a free intermediate Bos taurus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 enzyme participates in catabolism of tyrosine Sus scrofa homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 key enzyme involved in tyrosine catabolism, congenital 4-hydroxyphenylpyruvate dioxygenase deficiency is a rare, relatively benign condition known as hereditary type III tyrosinemia Homo sapiens homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 enzyme is involved in production of homogentisate, the aromatic precursor of all phenylquinones Daucus carota homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 4-hydroxyphenylpyruvate dioxygenase does not use phenolpyruvate as a substrate in normal plant metabolism Arabidopsis thaliana homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 hppD is transcriptionally activated by HpdA and repressed by HpdR Streptomyces coelicolor homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 the conversion of 4-hydroxyphenyl-pyruvate to homogentisate involves oxidative decarboxylation, side-chain migration and aromatic hydroxylation in a single catalytic cycle. The 4-HPPD reaction is unusual in that the 2-oxoacid and prime substrate moieties are contained within the same molecule Homo sapiens homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 second step of oxidative tyrosine catabolism Picrophilus torridus homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Pseudomonas fluorescens ATCC 13525 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Pseudomonas sp. P.J. 874 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Picrophilus torridus DSM 9790 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 second step of oxidative tyrosine catabolism Picrophilus torridus DSM 9790 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Streptomyces avermitilis ATCC 31267 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Shewanella oneidensis MR-1 / ATCC 700550 homogentisate + CO2 - ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Shewanella oneidensis MR-1 / ATCC 700550 homogentisate + CO2 homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin ? 260707 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Pseudomonas fluorescens 2,5-dihydroxyphenylacetate + CO2 - ? 407062 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Streptomyces avermitilis homogentisate + CO2 + 4-hydroxyphenylacetate the wild-type enzyme produces 85% homogentisate and 15% 4-hydroxyphenylacetate ? 424581 1.13.11.27 4-hydroxyphenylpyruvate + O2 - Streptomyces avermitilis homogentisate + CO2 + 4-hydroxyphenylacetate the wild-type enzyme produces 90% homogentisate, 1% quinolacetate, and 9% 4-hydroxyphenylacetate ? 424581 1.13.11.27 4-hydroxytetrafluorophenylpyruvate + O2 - Sus scrofa ? + CO2 - ? 260714 1.13.11.27 4-methylphenylpyruvate + O2 poor substrate Gallus gallus ? + CO2 - ? 260710 1.13.11.27 additional information Single turnover kinetics are observed spectrophotometrically by mixing equal volumes of the anaerobic enzyme-substrate complex and solutions containing molecular oxygen in the presence of saturating HPP using a stopped-flow spectrophotometer. k1 = 7.4 x 100000 /M/s, k2 = 74 /s, k3 = 13.2 /s, k4 = 1.6 /s, indicating the accumulation of three catalytic intermediates. The kinetic data observed with substrate substituted with deutererons for aromatic protons are not significantly different from those observed with the proteo substrate. The final phase in catalysis (k4), decreases to 0.7 /s in the presence of deuterium oxide solvent, indicating the involvement of a solvent-derived proton in this step. Streptomyces avermitilis ? - ? 89 1.13.11.27 additional information HpdR positively regulates hpdA expression through direct binding to the HpdA promoter within a region containing two conserved direct repeat sequences. HpdR-dependent hpdA transcription occurs in the presence of 4-hydroxyphenylpyruvate, tyrosine, and phenylalanine, as well as during starvation Sinorhizobium meliloti ? - ? 89 1.13.11.27 additional information no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate Picrophilus torridus ? - ? 89 1.13.11.27 additional information no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate Picrophilus torridus DSM 9790 ? - ? 89 1.13.11.27 phenylpyruvate + O2 - Gallus gallus 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 - Homo sapiens 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 - Rattus norvegicus 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 - Sus scrofa 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 - Pseudomonas sp. 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 at 10% of the activity with 4-hydroxyphenylpyruvate Sus scrofa 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 phenylpyruvate + O2 - Pseudomonas sp. P.J. 874 2-hydroxyphenylacetate + CO2 - ? 260708 1.13.11.27 [(4-hydroxyphenyl)thio]pyruvate + O2 substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed Pseudomonas sp. [(4-hydroxyphenyl)sulfinyl]acetate + CO2 - ? 260713 1.13.11.27 [(4-hydroxyphenyl)thio]pyruvate + O2 substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed Pseudomonas sp. P.J. 874 [(4-hydroxyphenyl)sulfinyl]acetate + CO2 - ? 260713