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Literature summary extracted from

  • Liu, B.; Falkenstein-Paul, H.; Schmidt, W.; Beerhues, L.
    Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional expression, and site-directed mutagenesis of two polyketide synthases (2003), Plant J., 34, 847-855.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
2.3.1.151 DTT required for maximum activity, without DTT the enzyme shows 40% of maximal activity Hypericum androsaemum

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.74 overexpression in Escherichia coli as glutathione-S-transferase fusion protein, wild-type and mutant enzymes: L263M, F265Y, G256A, S338G, L263M/F265Y, G256A/S338G, L263M/S338G, F265Y/S338G, L263M/F265Y/S338G, G256A/L263M/F265Y, G256A/L263M/F265Y/S338G Hypericum androsaemum
2.3.1.151 construction of cDNA library, DNA and amino acid sequence determination and analysis, functional overexpression of wild-type enzyme and expression of mutant enzymes in Escherichia coli strain BL21(DE3) as GST fusion protein Hypericum androsaemum

Protein Variants

EC Number Protein Variants Comment Organism
2.3.1.74 F265Y relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 7.2:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 F265Y/S338G relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 2.2:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 G256A relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 4.0:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 G256A/L263M/F265Y relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 12.5:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 G256A/L263M/F265Y/S338G relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 1.1:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 G256A/S338G relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 3.0:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 L263M relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 4.0:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 L263M/F265Y relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 3.7:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 L263M/F265Y/S338G mutant enzyme preferres benzoyl-CoA over 4-coumaroyl-CoA,relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 1.0:1.9 for the mutant enzyme Hypericum androsaemum
2.3.1.74 L263M/S338G relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 3.9:1 for the mutant enzyme Hypericum androsaemum
2.3.1.74 S338G relative activity with 4-coumaroyl-CoA and benzoyl-CoA as starter substrate is 4.5:1 for wild-type enzyme and 4.4:1 for the mutant enzyme Hypericum androsaemum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.74 0.0049
-
 4-coumaroyl-CoA pH 7.0, 35°C, wild-type enzyme Hypericum androsaemum
2.3.1.74 0.0054
-
 benzoyl-CoA pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G Hypericum androsaemum
2.3.1.74 0.0068
-
 benzoyl-CoA pH 7.0, 35°C, wild-type enzyme Hypericum androsaemum
2.3.1.74 0.0078
-
 4-coumaroyl-CoA pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G Hypericum androsaemum
2.3.1.74 0.0099
-
 malonyl-CoA pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G Hypericum androsaemum
2.3.1.74 0.0108
-
 malonyl-CoA pH 7.0, 35°C, wild-type enzyme Hypericum androsaemum
2.3.1.151 0.0057
-
 benzoyl-CoA pH 7.0, 35°C, recombinant enzyme Hypericum androsaemum
2.3.1.151 0.0231
-
 malonyl-CoA pH 7.0, 35°C, recombinant enzyme Hypericum androsaemum

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.151 42800
-
 2 * 42800, recombinant enzyme, SDS-PAGE Hypericum androsaemum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.151 benzoyl-CoA + 3 malonyl-CoA Hypericum androsaemum stepwise condensation, polyketid synthesis, benzoic acid biosynthetic pathway overview, the 3'-hydroxylation is catalyzed by a cytochrome P450 monooxygenase in Hypericum androsaemum 2,4,6-trihydroxybenzophenone + 4 CoA + 3 CO2
-
 ?
2.3.1.151 additional information Hypericum androsaemum benzoyl-CoA is a minor starter molecule of polyketid synthesis for PKS in other plants, phylogenetic analysis ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.74 Hypericum androsaemum
-
-
-
2.3.1.151 Hypericum androsaemum
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.151 DNA sequence determination and analysis, phylogenetic analysis, recombinant GST-tagged wild-type and mutant enzymes from Escherichia coli strain BL21(DE3), GST-tag is cleaved of by factor Xa Hypericum androsaemum

Reaction

EC Number Reaction Comment Organism Reaction ID
2.3.1.151 3 Malonyl-CoA + 3-hydroxybenzoyl-CoA = 4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2 reaction mechanism, multiple decarboxylative condensation with malonyl-CoA followed by cyclization and aromatization of the inter,ediate tetraketide Hypericum androsaemum
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.151 cell culture
-
 Hypericum androsaemum
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.74 4-coumaroyl-CoA + 3 malonyl-CoA
-
 Hypericum androsaemum naringenin chalcone + 4 CoA + 3 CO2
-
 ?
2.3.1.74 cinnamoyl-CoA + malonyl-CoA 87.5% of the activity with 4-coumaroyl-CoA + malonyl-CoA Hypericum androsaemum 5,7-dihydroxyflavanone + CoA + CO2
-
 ?
2.3.1.74 malonyl-CoA + 3-coumaroyl-CoA 34.4% of the activity with 4-coumaroyl-CoA + malonyl-CoA Hypericum androsaemum ? + CO2 + CoA
-
 ?
2.3.1.74 malonyl-CoA + 3-hydroxybenzoyl-CoA 21.8% of the activity with 4-coumaroyl-CoA + malonyl-CoA Hypericum androsaemum ? + CO2 + CoA
-
 ?
2.3.1.74 malonyl-CoA + benzoyl-CoA 22.3% of the activity with 4-coumaroyl-CoA + malonyl-CoA Hypericum androsaemum phlorobenzophenone + CO2 + CoA
-
 ?
2.3.1.151 3-hydroxybenzoyl-CoA + 3 malonyl-CoA low activity, stepwise condensation Hypericum androsaemum 2,3',4,6-tetrahydroxybenzophenone + 4 CoA + 3 CO2
-
 ?
2.3.1.151 4-hydroxybenzoyl-CoA + 3 malonyl-CoA very low activity, stepwise condensation Hypericum androsaemum 2,4,4',6-trihydroxybenzophenone + 4 CoA + 3 CO2
-
 ?
2.3.1.151 benzoyl-CoA + 3 malonyl-CoA stepwise condensation, polyketid synthesis, benzoic acid biosynthetic pathway overview, the 3'-hydroxylation is catalyzed by a cytochrome P450 monooxygenase in Hypericum androsaemum Hypericum androsaemum 2,4,6-trihydroxybenzophenone + 4 CoA + 3 CO2
-
 ?
2.3.1.151 benzoyl-CoA + 3 malonyl-CoA preferred substrate, stepwise condensation Hypericum androsaemum 2,4,6-trihydroxybenzophenone + 4 CoA + 3 CO2
-
 ?
2.3.1.151 additional information benzoyl-CoA is a minor starter molecule of polyketid synthesis for PKS in other plants, phylogenetic analysis Hypericum androsaemum ?
-
 ?
2.3.1.151 additional information no activity with activated cinnamic acids as starter compounds, e.g. 2-hydroxybenzoyl-CoA, 4-coumaroyl-CoA, 3-coumaroyl-CoA, 2-coumaroyl-CoA, cinnamoyl-CoA, caffeoyl-CoA, and feruloyl-CoA, no activity with acetyl-CoA, substrate specificity, overview Hypericum androsaemum ?
-
 ?
2.3.1.151 N-methylanthraniloyl-CoA + malonyl-CoA low activity, stepwise condensation Hypericum androsaemum ? + CoA + CO2
-
 ?

Subunits

EC Number Subunits Comment Organism
2.3.1.151 dimer 2 * 42800, recombinant enzyme, SDS-PAGE Hypericum androsaemum

Synonyms

EC Number Synonyms Comment Organism
2.3.1.74 chalcone synthase
-
 Hypericum androsaemum
2.3.1.151 BPS
-
 Hypericum androsaemum
2.3.1.151 More enzyme belongs to the plant polyketid synthase superfamily, i.e. type III PKSs Hypericum androsaemum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.151 35
-
-
 Hypericum androsaemum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.74 0.007
-
 4-coumaroyl-CoA pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G Hypericum androsaemum
2.3.1.74 0.0113
-
 benzoyl-CoA pH 7.0, 35°C, wild-type enzyme Hypericum androsaemum
2.3.1.74 0.0156
-
 benzoyl-CoA pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G Hypericum androsaemum
2.3.1.74 0.042
-
 4-coumaroyl-CoA pH 7.0, 35°C, wild-type enzyme Hypericum androsaemum
2.3.1.151 9.66
-
 benzoyl-CoA pH 7.0, 35°C, recombinant enzyme Hypericum androsaemum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.151 6.5 7
-
 Hypericum androsaemum