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Information on EC 1.13.11.27 - 4-hydroxyphenylpyruvate dioxygenase and Organism(s) Rattus norvegicus and UniProt Accession P32755

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IUBMB Comments
The Pseudomonas enzyme contains one Fe3+ per mole of enzyme; the enzymes from other sources may contain essential iron or copper.
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This record set is specific for:
Rattus norvegicus
UNIPROT: P32755
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The taxonomic range for the selected organisms is: Rattus norvegicus
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
f protein, 4-hydroxyphenylpyruvate dioxygenase, tf-ag, p-hydroxyphenylpyruvate dioxygenase, 4-hppd, 4-hydroxyphenylpyruvic acid dioxygenase, 4hppd, athppd, p-hydroxyphenylpyruvate hydroxylase, legiolysin, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4-HPPD
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-
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4-hydroxyphenylpyruvic acid dioxygenase
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4HPPD
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EC 1.14.2.2
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EC 1.99.1.14, formerly
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-
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F Alloantigen
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F protein
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F-antigen homolog
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-
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HPD
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HPPD
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HPPDase
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Legiolysin
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oxygenase, 4-hydroxyphenylpyruvate di-
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p-hydroxyphenylpyruvate dioxygenase
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p-hydroxyphenylpyruvate hydroxylase
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p-hydroxyphenylpyruvate oxidase
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p-hydroxyphenylpyruvic acid hydroxylase
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p-hydroxyphenylpyruvic hydroxylase
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p-hydroxyphenylpyruvic oxidase
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T-cell reactive protein
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TF-AG
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-
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
show the reaction diagram
reaction mechanism, quantum and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
decarboxylation
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redox reaction
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hydroxylation
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side-chain migration
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-
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxyphenylpyruvate:oxygen oxidoreductase (hydroxylating, decarboxylating)
The Pseudomonas enzyme contains one Fe3+ per mole of enzyme; the enzymes from other sources may contain essential iron or copper.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-72-5
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
show the reaction diagram
-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
show the reaction diagram
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-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
show the reaction diagram
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-
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-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
show the reaction diagram
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-
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
required for catalysis, mechanism, overview
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
50% inhibition below 20 nM
DAS 645
low inhibition
DAS 869
strong inhibition
mesotrione
low inhibition
NTBC
tauromers, strong inhibition of the two tautomers
sulcotrione
low inhibition
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
rapid inactivation of the enzyme by the formation of an enzyme-inhibitor complex that dissociates with recovery of enzyme activity
2-[2-nitro-4-(trifluoromethyl)benzoyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione
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50 nM, 50% inhibition, tight-binding reversible inhibitor, rapid inactivation by the formation of an enzyme-inhibitor complex that dissociates extremely slowly with recovery of enzyme activity
4-hydroxyphenylpyruvate
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o-hydroxyphenylpyruvate
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competitive inhibitor of 4-hydroxyphenylpyruvate
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
3,4-Dihydroxyphenylpyruvate
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0.05
4-hydroxyphenylpyruvate
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0.06
phenylpyruvate
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00002
DAS 645
Rattus norvegicus
below, pH and temperature not specified in the publication
0.00004
NTBC
Rattus norvegicus
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
methods for assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
abundantly expressed in neurons of
Manually annotated by BRENDA team
abundantly expressed in neurons of
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
enzyme molecular docking study using crystal structure PDB ID 1SQI
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
HPPD_RAT
393
0
45112
Swiss-Prot
Mitochondrion (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
x * 44000, SDS-PAGE and deduced from gene sequence
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 44000, SDS-PAGE and deduced from gene sequence
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
undergoes both N-and C-terminal processing, C-terminal processing enhances enzymic activity
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
with and without inhibitors 1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole or [1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Abbott, M.T.; Udenfriend, S.
alpha-Ketoglutarate-coupled dioxygenases
Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York
167-214
1974
Bos taurus, Canis lupus familiaris, Cavia porcellus, Gallus gallus, Oryctolagus cuniculus, Frog, Homo sapiens, Platyrrhini, Oncorhynchus mykiss, Didelphidae, Rattus norvegicus, Sus scrofa
-
Manually annotated by BRENDA team
Fellman, J.H.; Fujita, T.S.; Roth, E.S.
Assay, properties and tissue distribution of p-hydroxyphenylpyruvate hydroxylase
Biochim. Biophys. Acta
284
90-100
1972
Platyrrhini, Oncorhynchus mykiss, Didelphidae, Rattus norvegicus
Manually annotated by BRENDA team
Ellis, M.K.; Whitfield, A.C.; Gowans, L.A.; Auton, T.R.; Provan, W.M.; Lock, E.A.; Lee, D.L.; Smith, L.L.
Characterization of the interaction of 2-[2-nitro-4-(trifluoromethyl)benzoyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione with rat hepatic 4-hydroxyphenylpyruvate dioxygenase
Chem. Res. Toxicol.
9
24-27
1996
Rattus norvegicus
Manually annotated by BRENDA team
Ellis, M.K.; Whitfield, A.C.; Gowans, L.A.; Auton, T.R.; Provan, W.M.; Lock, E.A.; Smith, L.L.
Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione
Toxicol. Appl. Pharmacol.
133
12-19
1995
Rattus norvegicus
Manually annotated by BRENDA team
Yang, C.; Pflugrath, J.W.; Camper, D.L.; Foster, M.L.; Pernich, D.J.; Walsh, T.A.
Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases
Biochemistry
43
10414-10423
2004
Rattus norvegicus (P32755), Arabidopsis thaliana (P93836), Arabidopsis thaliana
Manually annotated by BRENDA team
Neve, S.; Aarenstrup, L.; Tornehave, D.; Rahbek-Nielsen, H.; Corydon, T.J.; Roepstorff, P.; Kristiansen, K.
Tissue distribution, intracellular localization and proteolytic processing of rat 4-hydroxyphenylpyruvate dioxygenase
Cell Biol. Int.
27
611-624
2003
Rattus norvegicus (P32755)
Manually annotated by BRENDA team
Silva, T.; Dos Santos Pires, M.; De Castro, A.; Da Cunha, E.; Caetano, M.; Ramalho, T.
Molecular insight into the inhibition mechanism of plant and rat 4-hydroxyphenylpyruvate dioxygenase by molecular docking and DFT calculations
Med. Chem. Res.
24
3958-3971
2015
Rattus norvegicus (P32755), Arabidopsis thaliana (P93836)
-
Manually annotated by BRENDA team