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Literature summary extracted from

  • Xu, J.; Fang, X.; Li, C.; Zhao, Q.; Martin, C.; Chen, X.; Yang, L.
    Characterization of Arabidopsis thaliana hydroxyphenylpyruvate reductases in the tyrosine conversion pathway (2018), Front. Plant Sci., 9, 1305 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.81 isozyme HPPR2, sequence comparisons and phylogenetic analysis, quantitative reverse transcription PCR enzyme expression analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain Rose-gami B (DE3). Recombinant expression of GFP-tagged enzyme in Arabidopsis thaliana protoplasts Arabidopsis thaliana
1.1.1.237 isozyme HPPR3, sequence comparisons and phylogenetic analysis, quantitative reverse transcription PCR enzyme expression analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain Rose-gami B (DE3). Recombinant expression of GFP-tagged enzyme in Arabidopsis thaliana protoplasts Arabidopsis thaliana

Protein Variants

EC Number Protein Variants Comment Organism
1.1.1.81 additional information expression analysis of HPPR2, HPPR3, and other pathway-related enzymes in mutant strains, HPPR2 mutant phenotype, overview Arabidopsis thaliana
1.1.1.237 additional information expression analysis of HPPR2, HPPR3, and other pathway-related enzymes in mutant strains, HPPR3 mutant phenotype, overview Arabidopsis thaliana

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.81 0.8
-
 4-hydroxyphenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 1.05
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 1.05
-
 Hydroxypyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 1.5 2 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 3.57
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 3.7
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 3.7
-
 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.37
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.37
-
 3-(4-hydroxyphenyl)pyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.8
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 1.5 2 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 1.5 2 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 3.57
-
 Hydroxypyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 3.7
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.1.1.81 cytosol
-
 Arabidopsis thaliana 5829
-
1.1.1.237 cytosol
-
 Arabidopsis thaliana 5829
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.81 4-hydroxyphenylpyruvate + NADPH + H+ Arabidopsis thaliana
-
 3-(4-hydroxyphenyl)lactate + NADP+
-
 ?
1.1.1.81 hydroxypyruvate + NADPH + H+ Arabidopsis thaliana
-
 D-glycerate + NADP+
-
 r
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+ Arabidopsis thaliana
-
 (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+ Arabidopsis thaliana Col-0
-
 (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.81 Arabidopsis thaliana A0A178WMD4 catalyzes reactions of EC 1.1.1.79 and EC 1.1.1.81
-
1.1.1.81 Arabidopsis thaliana Q9CA90
-
-
1.1.1.81 Arabidopsis thaliana Q9CA90 catalyzes reactions of EC 1.1.1.237 and EC 1.1.1.81
-
1.1.1.81 Arabidopsis thaliana Col-0 Q9CA90
-
-
1.1.1.237 Arabidopsis thaliana A0A178WMD4 catalyzes reactions of EC 1.1.1.79, EC 1.1.1.81, EC 1.1.1.237
-
1.1.1.237 Arabidopsis thaliana Q9CA90 catalyzes reactions of EC 1.1.1.237 and EC 1.1.1.81
-
1.1.1.237 Arabidopsis thaliana Q9LE33
-
-
1.1.1.237 Arabidopsis thaliana Col-0 Q9LE33
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.81 recombinant His-tagged enzyme from Escherichia coli strain Rose-gami B (DE3) by nickel affinity chromatography and desalting gel filtration Arabidopsis thaliana
1.1.1.237 recombinant His-tagged enzyme from Escherichia coli strain Rose-gami B (DE3) by nickel affinity chromatography and desalting gel filtration Arabidopsis thaliana

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.81 cauline leaf
-
 Arabidopsis thaliana
-
1.1.1.81 flower
-
 Arabidopsis thaliana
-
1.1.1.81 additional information high overall expression in seedling Arabidopsis thaliana
-
1.1.1.81 additional information quantitative reverse transcription PCR enzyme expression analysis Arabidopsis thaliana
-
1.1.1.81 rosette leaf
-
 Arabidopsis thaliana
-
1.1.1.81 seedling
-
 Arabidopsis thaliana
-
1.1.1.81 stamen of young flowers Arabidopsis thaliana
-
1.1.1.81 stem
-
 Arabidopsis thaliana
-
1.1.1.81 trichome
-
 Arabidopsis thaliana
-
1.1.1.237 flower
-
 Arabidopsis thaliana
-
1.1.1.237 additional information high overall expression in seedling Arabidopsis thaliana
-
1.1.1.237 additional information quantitative reverse transcription PCR enzyme expression analysis Arabidopsis thaliana
-
1.1.1.237 rosette leaf
-
 Arabidopsis thaliana
-
1.1.1.237 seedling
-
 Arabidopsis thaliana
-
1.1.1.237 stamen of young flowers Arabidopsis thaliana
-
1.1.1.237 stem
-
 Arabidopsis thaliana
-
1.1.1.237 stem leaf
-
 Arabidopsis thaliana
-
1.1.1.237 trichome
-
 Arabidopsis thaliana
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.81 4-hydroxyphenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana 3-(4-hydroxyphenyl)lactate + NADP+
-
 ?
1.1.1.81 4-hydroxyphenylpyruvate + NADPH + H+ reaction of EC 1.1.1.237 Arabidopsis thaliana 3-(4-hydroxyphenyl)lactate + NADP+
-
 ?
1.1.1.81 hydroxypyruvate + NADPH + H+
-
 Arabidopsis thaliana D-glycerate + NADP+
-
 ?
1.1.1.81 hydroxypyruvate + NADPH + H+
-
 Arabidopsis thaliana D-glycerate + NADP+
-
 r
1.1.1.81 hydroxypyruvate + NADPH + H+ best substrate Arabidopsis thaliana D-glycerate + NADP+
-
 r
1.1.1.81 additional information isoform HPPR2 has both hydroxyphenylpyruvate reductase and hydroxypyruvate reductase activities Arabidopsis thaliana ?
-
-
1.1.1.81 additional information isoform HPPR2 has both hydroxyphenylpyruvate reductase and hydroxypyruvate reductase activities Arabidopsis thaliana Col-0 ?
-
-
1.1.1.81 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana D-phenyllactate + NADP+
-
 ?
1.1.1.81 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana phenyllactate + NADP+
-
 ?
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+
-
 Arabidopsis thaliana (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+ best substrate Arabidopsis thaliana (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+
-
 Arabidopsis thaliana Col-0 (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r
1.1.1.237 3-(4-hydroxyphenyl)pyruvate + NADPH + H+ best substrate Arabidopsis thaliana Col-0 (R)-3-(4-hydroxyphenyl)lactate + NADP+
-
 r
1.1.1.237 4-hydroxyphenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana 3-(4-hydroxyphenyl)lactate + NADP+
-
 ?
1.1.1.237 4-hydroxyphenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana Col-0 3-(4-hydroxyphenyl)lactate + NADP+
-
 ?
1.1.1.237 hydroxypyruvate + NADPH + H+
-
 Arabidopsis thaliana D-glycerate + NADP+
-
 ?
1.1.1.237 hydroxypyruvate + NADPH + H+ reaction of EC 1.1.1.81 Arabidopsis thaliana D-glycerate + NADP+
-
 ?
1.1.1.237 hydroxypyruvate + NADPH + H+ reaction of EC 1.1.1.81 Arabidopsis thaliana Col-0 D-glycerate + NADP+
-
 ?
1.1.1.237 hydroxypyruvate + NADPH + H+
-
 Arabidopsis thaliana Col-0 D-glycerate + NADP+
-
 ?
1.1.1.237 additional information isoform HPPR2 has both hydroxyphenylpyruvate reductase and hydroxypyruvate reductase activities Arabidopsis thaliana ?
-
-
1.1.1.237 additional information isoform HPPR2 has both hydroxyphenylpyruvate reductase and hydroxypyruvate reductase activities Arabidopsis thaliana Col-0 ?
-
-
1.1.1.237 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana D-phenyllactate + NADP+
-
 ?
1.1.1.237 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana Col-0 D-phenyllactate + NADP+
-
 ?
1.1.1.237 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana phenyllactate + NADP+
-
 ?
1.1.1.237 phenylpyruvate + NADPH + H+
-
 Arabidopsis thaliana Col-0 phenyllactate + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.81 At1g79870
-
 Arabidopsis thaliana
1.1.1.81 AXX17_At1g12940
-
 Arabidopsis thaliana
1.1.1.81 HPPR2
-
 Arabidopsis thaliana
1.1.1.81 HPPR3
-
 Arabidopsis thaliana
1.1.1.81 HPR2
-
 Arabidopsis thaliana
1.1.1.81 HPR3
-
 Arabidopsis thaliana
1.1.1.81 More cf. EC 1.1.1.237 Arabidopsis thaliana
1.1.1.237 At1g12940
-
 Arabidopsis thaliana
1.1.1.237 At1g79870
-
 Arabidopsis thaliana
1.1.1.237 HPPR2
-
 Arabidopsis thaliana
1.1.1.237 HPPR3
-
 Arabidopsis thaliana
1.1.1.237 HPR2
-
 Arabidopsis thaliana
1.1.1.237 HPR3
-
 Arabidopsis thaliana

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.81 30
-
 assay at Arabidopsis thaliana
1.1.1.237 30
-
 assay at Arabidopsis thaliana

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.81 0.033
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.033
-
 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 0.05
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.122
-
 4-hydroxyphenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 0.61
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.927
-
 Hydroxypyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 0.93
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.033
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.052
-
 Hydroxypyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.122
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.28
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.285
-
 3-(4-hydroxyphenyl)pyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.61
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.611
-
 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.81 7
-
 assay at Arabidopsis thaliana
1.1.1.237 7
-
 assay at Arabidopsis thaliana

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.81 NADPH
-
 Arabidopsis thaliana
1.1.1.237 NADPH
-
 Arabidopsis thaliana

General Information

EC Number General Information Comment Organism
1.1.1.81 evolution no hydroxyphenylpyruvate reductase (HPPR) activity by isozyme HPPR4 from Arabidopsis thaliana. Isozyme HPPR2 mainly shows hydroxypyruvate reductase (HPR) activity, while isozyme HPPR3 mainly shows 4-hydroxyphenylpyruvate reductase (EC 1.1.1.237) activity. Enzyme HPPR2 belongs to the family of D-isomer-specific 2-hydroxyacid dehydrogenases, group II Arabidopsis thaliana
1.1.1.81 malfunction Arabidopsis thaliana mutants defective in either HPPR2 or HPPR3 isozyme contain lower amounts of pHPL and are impaired in conversion of tyrosine to pHPL. Furthermore, a loss-of-function mutation in tyrosine aminotransferase (TAT) also reduces the pHPL accumulation in plants Arabidopsis thaliana
1.1.1.81 metabolism in vitro characterization of the recombinant proteins reveals that HPPR2 has both hydroxypyruvate reductase (HPR EC 1.1.1.81, main activity) and hydroxyphenylpyruvate reductase (HPPR, EC 1.1.1.237) activities, whereas HPPR3 has a strong preference for pHPP, and both enzymes are localized in the cytosol. In Arabidopsis thaliana, HPPR2 and HPPR3, together with tyrosine aminotransferase 1 (TAT1), constitute to a probably conserved biosynthetic pathway from tyrosine to 4-hydroxyphenyllactic acid (pHPL), from which some specialized metabolites, such as rosmarinic acid (RA), can be generated in specific groups of plants. Role of HPPR in the tyrosine conversion pathway, overview Arabidopsis thaliana
1.1.1.81 physiological function Arabidopsis mutants defective in either isoform HPPR2 or HPPR3 contain lower amounts of 4-hydroxyphenyllactic acid and are impaired in conversion of tyrosine to 4-hydroxyphenyllactic acid Arabidopsis thaliana
1.1.1.81 physiological function hydroxyphenylpyruvate reductase (HPPR), which catalyzes the reduction of 4-hydroxyphenylpyruvic acid (pHPP) to 4-hydroxyphenyllactic acid (pHPL), is the key enzyme in the biosynthesis of rosmarinic acid (RA) from tyrosine and, so far, HPPR activity is reported only from the RA-accumulating plants Arabidopsis thaliana
1.1.1.237 evolution no hydroxyphenylpyruvate reductase (HPPR) activity by isozyme HPPR4 from Arabidopsis thaliana. Isozyme HPPR2 mainly shows hydroxypyruvate reductase (HPR) activity (EC 1.1.1.81), while isozyme HPPR3 mainly shows 4-hydroxyphenylpyruvate reductase activity. Enzyme HPPR3 belongs to the family of D-isomer-specific 2-hydroxyacid dehydrogenases, group II Arabidopsis thaliana
1.1.1.237 malfunction Arabidopsis thaliana mutants defective in either HPPR2 or HPPR3 isozyme contain lower amounts of pHPL and are impaired in conversion of tyrosine to pHPL. Furthermore, a loss-of-function mutation in tyrosine aminotransferase (TAT) also reduces the pHPL accumulation in plants. HPR mutants show impaired growth and contain less chlorophyll, phenotypes, detailed overview Arabidopsis thaliana
1.1.1.237 metabolism in vitro characterization of the recombinant proteins reveals that HPPR2 has both hydroxypyruvate reductase (HPR EC 1.1.1.81) and hydroxyphenylpyruvate reductase (HPPR) activities, whereas HPPR3 has a strong preference for pHPP, and both enzymes are localized in the cytosol. In Arabidopsis thaliana, HPPR2 and HPPR3, together with tyrosine aminotransferase 1 (TAT1), constitute to a probably conserved biosynthetic pathway from tyrosine to 4-hydroxyphenyllactic acid (pHPL), from which some specialized metabolites, such as rosmarinic acid (RA), can be generated in specific groups of plants. Role of HPPR in the tyrosine conversion pathway, overview Arabidopsis thaliana
1.1.1.237 physiological function Arabidopsis mutants defective in either isoform HPPR2 or HPPR3 contain lower amounts of 4-hydroxyphenyllactic acid and are impaired in conversion of tyrosine to 4-hydroxyphenyllactic acid Arabidopsis thaliana
1.1.1.237 physiological function hydroxyphenylpyruvate reductase (HPPR), which catalyzes the reduction of 4-hydroxyphenylpyruvic acid (pHPP) to 4-hydroxyphenyllactic acid (pHPL), is the key enzyme in the biosynthesis of rosmarinic acid (RA) from tyrosine and, so far, HPPR activity is reported only from the RA-accumulating plants Arabidopsis thaliana

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.81 0.009
-
 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 0.009
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.015
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.153
-
 4-hydroxyphenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.81 0.4
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.81 0.95
-
 Hydroxypyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.009
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.157
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.4
-
 phenylpyruvate pH 7, 30°C Arabidopsis thaliana
1.1.1.237 0.402
-
 phenylpyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.77
-
 3-(4-hydroxyphenyl)pyruvate pH 7.0, 30°C, recombinant enzyme Arabidopsis thaliana
1.1.1.237 0.78
-
 4-hydroxyphenylpyruvate pH 7, 30°C Arabidopsis thaliana