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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
homogentisate
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
evidence against participation of a quinol as a free intermediate
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
enzyme form 3: ordered bi bi mechanism where 4-hydroxyphenylpyruvate is added prior to oxygen and CO2 released before homogentisate
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
in plants this enzyme activity is involved in two distinct metabolic processes, the biosynthesis of prenylquinones and the catabolism of tyrosine
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
rate-determining step in catalysis is a protein conformation change
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mono-iso-ordered bi-bi mechanism with binding of 4-hydroxyphenylpyruvate before O2 and release of CO2 before homogentisate. A Theorell-Chance mechanism can not be excluded
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
addition of substrate and oxygen to the holoenzyme is formally random, holo-enzym in complex with substrate has a 3600-fold increase in oxygen reactivity
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mechanism of oxygen binding and activation, structural relationship to other dioxygenases
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
ternary enzyme-substrate complex is firstly decarboxylated to the iron(II)-peracid intermediate followed by heterolytic cleavage of the O-O bond yielding an iron(IV)-oxospecies. This attacks the aromatic ring in C1 position. The arene oxide has no catalytic relevance
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
the C-terminal helix forms a gate for substrate access to the active site around a nonheme ferrous iron center
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
the C-terminal helix forms a gate for substrate access to the active site around a nonheme ferrous iron center, completely sequestering the active site from solvent
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, overview
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
The data of the rapid acid quench followd by HPLC product analysis, indicate that the homogenisate product is formed during one turnover, as the amount of product is equivalent to the enzyme-substrate complex at 191 ms.
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, inhibitor-bound crystal structure, PDB ID 1CJX, analysis, detailed overview
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum mechanics/molecular mechanics calculations and simulations, detailed overview
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum mechanics/molecular mechanics calculations and simulations, detailed overview
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mono-iso-ordered bi-bi mechanism with binding of 4-hydroxyphenylpyruvate before O2 and release of CO2 before homogentisate. A Theorell-Chance mechanism can not be excluded
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4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
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(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
(4-hydroxyphenyl)-pyruvate + O2
homogentisate + CO2
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-
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-
?
2-thienylpyruvate + O2
? + CO2
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-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
3-thienylpyruvate + O2
3-carboxymethyl-3-thiolene-2-one + CO2
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-
-
?
4-fluorophenylpyruvate + O2
4-fluoro-2-hydroxyphenylacetate + CO2
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-
-
-
?
4-hydroxyphenylpyruvate + O2
2,5-dihydroxyphenylacetate + CO2
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-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
4-hydroxytetrafluorophenylpyruvate + O2
? + CO2
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-
?
4-methylphenylpyruvate + O2
? + CO2
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poor substrate
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?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
additional information
?
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(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
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?
(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
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-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
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-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
4-hydroxyphenylpyruvate dioxygenase does not use phenolpyruvate as a substrate in normal plant metabolism
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
evidence against participation of a quinol as a free intermediate
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
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-
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
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-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme is involved in production of homogentisate, the aromatic precursor of all phenylquinones
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
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-
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Frog
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
activity with the keto-form of 4-hydroxyphenylpyruvate is 40times higher than with the enol tautomer
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
key enzyme involved in tyrosine catabolism, congenital 4-hydroxyphenylpyruvate dioxygenase deficiency is a rare, relatively benign condition known as hereditary type III tyrosinemia
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
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
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
hppD is transcriptionally activated by HpdA and repressed by HpdR
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
best substrate
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme participates in catabolism of tyrosine
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
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the wild-type enzyme produces 85% homogentisate and 15% 4-hydroxyphenylacetate
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?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
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the wild-type enzyme produces 90% homogentisate, 1% quinolacetate, and 9% 4-hydroxyphenylacetate
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?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
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-
-
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?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
at 10% of the activity with 4-hydroxyphenylpyruvate
-
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?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
-
substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed
-
-
?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
1.13.11.27 4-hydroxyphenylpyruvate dioxygenase
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