Information on EC 1.1.1.237 - hydroxyphenylpyruvate reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.237
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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
-
-
-
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redox reaction
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-
-
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reduction
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
4-hydroxybenzoate biosynthesis I (eukaryotes)
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rosmarinic acid biosynthesis II
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suberin monomers biosynthesis
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Ubiquinone and other terpenoid-quinone biosynthesis
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Tyrosine metabolism
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Phenylalanine metabolism
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Tropane, piperidine and pyridine alkaloid biosynthesis
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Biosynthesis of secondary metabolites
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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
cv. Tigullio, a commercial cultivar of sweet basil
UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
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
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r
3,4-dihydroxyphenylpyruvate + NADPH + H+
3,4-dihydroxyphenyllactate + NADP+
show the reaction diagram
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-
-
?
3,4-dihydroxyphenylpyruvate + NADPH + H+
3-(3,4-dihydroxyphenyl)lactate + NADP+
show the reaction diagram
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-
-
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
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
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-
-
-
?
4-hydroxyphenylpyruvate + NADH
3-(4-hydroxyphenyl)lactate + NAD+
show the reaction diagram
4-hydroxyphenylpyruvate + NADPH + H+
4-hydroxyphenyllactate + NADP+
show the reaction diagram
4-hydroxyphenylpyruvate + NADPH + H+
D-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
glyoxylate + NADPH + H+
glycolate + 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
?
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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 + NADH + H+
3-(4-hydroxyphenyl)lactate + NAD+
show the reaction diagram
3-(4-hydroxyphenyl)pyruvate + NADPH + H+
3-(4-hydroxyphenyl)lactate + NADP+
show the reaction diagram
Q65CJ7
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?
4-hydroxyphenylpyruvate + NADPH + H+
4-hydroxyphenyllactate + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
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
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substrate inhibition
Fe2+
1 mM, less than 10% residual activity
Hg2+
1 mM, less than 10% residual activity
oxaloacetate
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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
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prevents oxidation of substrates
L-tyrosine
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activates the enzyme
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
130
3,4-Dihydroxyphenylpyruvate
250
3-methoxy-4-hydroxyphenylpyruvate
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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
pH 6.5, 25C
73
hydroxyphenylpyruvate
pH 6.5, 25C
9.1
Hydroxypyruvate
pH 6.5, 25C
31
NADH
pH 6.5, 25C
121
NADPH
pH 6.5, 25C
150
phenylpyruvate
pH 6.5, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
glyoxylate
pH 6.5, 25C
110
hydroxyphenylpyruvate
pH 6.5, 25C
2.6
Hydroxypyruvate
pH 6.5, 25C
310
NADH
pH 6.5, 25C
12000
NADPH
pH 6.5, 25C
380
phenylpyruvate
pH 6.5, 25C
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
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.58
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high enzyme activity
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34000
2 * 34000, SDS-PAGE
34110
calculation from amino acid sequence
40000
2 * 40000, SDS-PAGE, 2 * 40300, calculated
40300
2 * 40000, SDS-PAGE, 2 * 40300, calculated
45000 - 68000
gel filtration
75000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
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
gene CbHPPR, DNA and amino acid sequence determination and analysis, hairy root lines of Coleus blumei carrying HPPR RNAi suppression and overexpression constructs are established using Agrobacterium rhizogenes strain LBA15834-mediated transformation, HPPR is overexpressed under control of the constitutive CaMV 35S-promoter
gene HPPR, quantitative real-time reverse transcription PCR enzyme expression analysis
gene PfHPPR, DNA and amino acid sequence determination and analysis, sequence comparisons, quantitative real-time PCR enzyme expression analysis
gene SbHPPR, DNA and amino acid sequence determination and analysis, sequence comparisons, quantitative real-time PCR enzyme expression analysis
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gene SmHPPR, semiquantitative RT-PCR enzyme expression analysis
gene SoHPPR, DNA and amino acid sequence determination and analysis, sequence comparisons, quantitative RT-PCR enzyme expression analysis
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
basil plant inoculation with either the arbuscular mycorrhizal fungus (AMF) species Rhizophagus intraradices or a combination of two plant growth-promoting (PGP) isolated from its sporosphere, Sinorhizobium meliloti TSA41 and Streptomyces sp. W43N, triggers the overexpression hydroxyphenylpyruvate reductase (HPPR) and other genes encoding enzymes in volved in the rosmiarinic acid biosynthesis, overview. Levels of HPPR downstream of TAT are upregulated 2fold in leaves produced by plants inoculated with bacteria, while in mycorrhizal plants, they are downregulated
expression of PfHPPR can be induced by several factors such as abscisic acid (ABA), salicylic acid (SA), and ultraviolet-B radiation (UV-B)
levels of HPPR downstream of TAT are upregulated 2fold in leaves produced by plants inoculated with bacteria, while in mycorrhizal plants, they are downregulated
methyljasmonate, salicylic acid, gibberellic acid 3, and abscisic acid treatments upregulate SmHPPR transcription level
presence of phenylalanine results in up to 40fold increase in transcripts
UV-B radiation and hydrogen peroxide treatments downregulate SmHPPR transcription level
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information