Information on EC 1.1.1.237 - hydroxyphenylpyruvate reductase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
1.1.1.237
-
RECOMMENDED NAME
GeneOntology No.
hydroxyphenylpyruvate reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3-(4-hydroxyphenyl)lactate + NAD+ = 3-(4-hydroxyphenyl)pyruvate + NADH + H+
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
4-hydroxybenzoate biosynthesis I (eukaryotes)
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-
Biosynthesis of secondary metabolites
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-
Phenylalanine metabolism
-
-
rosmarinic acid biosynthesis II
-
-
suberin monomers biosynthesis
-
-
Tropane, piperidine and pyridine alkaloid biosynthesis
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Tyrosine metabolism
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Ubiquinone and other terpenoid-quinone biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
4-hydroxyphenyllactate:NAD+ oxidoreductase
Also acts on 3-(3,4-dihydroxyphenyl)lactate. Involved with EC 2.3.1.140 rosmarinate synthase in the biosynthesis of rosmarinic acid.
CAS REGISTRY NUMBER
COMMENTARY hide
117590-77-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the family of D-isomer-specific 2-hydroxyacid dehydrogenases
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,4-dihydroxyphenylpyruvate + NADH
3-(3,4-dihydroxyphenyl)lactate + NAD+
show the reaction diagram
3,4-dihydroxyphenylpyruvate + NADH + H+
3-(3,4-dihydroxyphenyl)lactate + NAD+
show the reaction diagram
-
-
-
r
3,4-dihydroxyphenylpyruvate + NADPH + H+
3,4-dihydroxyphenyllactate + NADP+
show the reaction diagram
-
-
-
?
3,4-dihydroxyphenylpyruvate + NADPH + H+
3-(3,4-dihydroxyphenyl)lactate + NADP+
show the reaction diagram
-
-
-
r
3-(4-hydroxyphenyl)lactate + NAD+
4-hydroxyphenylpyruvate + NADH
show the reaction diagram
3-(4-hydroxyphenyl)pyruvate + NADH + H+
3-(4-hydroxyphenyl)lactate + NAD+
show the reaction diagram
-
-
-
r
3-(4-hydroxyphenyl)pyruvate + NADPH + H+
3-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
3-methoxy-4-hydroxyphenylpyruvate + NADH
3-(3-methoxy-4-hydroxyphenyl)lactate + NAD+
show the reaction diagram
-
-
-
-
?
4-hydroxyphenylpyruvate + NADH
3-(4-hydroxyphenyl)lactate + NAD+
show the reaction diagram
4-hydroxyphenylpyruvate + NADPH + H+
4-hydroxyphenyllactate + NADP+
show the reaction diagram
glyoxylate + NADPH + H+
glycolate + NADP+
show the reaction diagram
hydroxyphenylpyruvate + NADPH + H+
D-hydroxyphenyllactate + NADP+
show the reaction diagram
hydroxypyruvate + NADH + H+
D-glycerate + NAD+
show the reaction diagram
phenylpyruvate + NADPH + H+
D-phenyllactate + NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3-(4-hydroxyphenyl)lactate + NAD+
4-hydroxyphenylpyruvate + NADH
show the reaction diagram
3-(4-hydroxyphenyl)pyruvate + NADPH + H+
3-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
Q65CJ7
-
-
-
?
4-hydroxyphenylpyruvate + NADPH + H+
4-hydroxyphenyllactate + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
NADPH is preferred over NADH
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-hydroxyphenylpyruvate
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substrate inhibition
Cu2+
1 mM, less than 10% residual activity
dihydroxyphenylpyruvate
-
substrate inhibition
Fe2+
1 mM, less than 10% residual activity
Hg2+
1 mM, less than 10% residual activity
oxaloacetate
-
inhibition at 5 mM
p-Coumaroyl-CoA
pyruvate
rosmarinic acid
WO42-
1 mM, less than 10% residual activity
Zn2+
1 mM, less than 10% residual activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbic acid
-
prevents oxidation of substrates
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
130
3,4-Dihydroxyphenylpyruvate
250
3-methoxy-4-hydroxyphenylpyruvate
-
pH 7
10
4-hydroxyphenylpyruvate
18.9
glyoxylate
pH 6.5, 25C
0.64
hydroxyphenylpyruvate
pH 6.5, 25C
3.5
Hydroxypyruvate
pH 6.5, 25C
0.1 - 190
NADH
0.01 - 95
NADPH
0.4
phenylpyruvate
pH 6.5, 25C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
19
glyoxylate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
73
hydroxyphenylpyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
9.1
Hydroxypyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
31
NADH
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
121
NADPH
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
150
phenylpyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
glyoxylate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
101
110
hydroxyphenylpyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
3899
2.6
Hydroxypyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
389
310
NADH
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
8
12000
NADPH
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
5
380
phenylpyruvate
Wickerhamia fluorescens
F1T2J9
pH 6.5, 25C
198
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Plectranthus scutellarioides
Plectranthus scutellarioides
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34110
calculation from amino acid sequence
45000 - 68000
gel filtration
75000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 34113, calculation from nucleotide sequence
homodimer
2 * 34113, sequence calculation and crystal structure
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
apoenzyme and enzyme in complex with NADP+, sitting drop vapour diffusion method, mixing of 0.001 ml of 6 mg/ml protein or 15 mg/ml protein with 2 mM NADP+ in 50 mM Tris-HCl, pH 7.0, with 0.001 ml of well solution containing 30% 2-methyl-2,4-pentanediol, 0.2 M NaCl, 0.1 M Tris-HCl, pH 7.5 at 4C, or 20% PEG 1000, 0.1 M imidazole, pH 7.5, 4 mM 4-hydroxyphenylpyruvate, 0.2 mM DTT at 26C, leading to one-crystal clusters or tetragonal bipyramid-shaped crystals, X-ray diffraction structure determination and analysis at 1.47 A and 2.2 A, respectively, modeling
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
sensitive to oxidation by light and oxygen
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, loss of 30% activity after 1 month
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-20C, loss of 85% activity after 10 weeks
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation and Sephadex G25 column
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recombinant N-terminally His-tagged enzyme from Escherichia coli strain BL21 (DE3) pLysS by nickel affinity and 2',5'-ADP affinity chromatography and dialysis
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
expression of N-terminally His-tagged enzyme in Escherichia coli strain BL21 (DE3) pLysS
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
presence of phenylalanine results in up to 40fold increase in transcripts