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Literature summary extracted from

  • Abe, I.; Abe, T.; Wanibuchi, K.; Noguchi, H.
    Enzymatic formation of quinolone alkaloids by a plant type III polyketide synthase (2006), Org. Lett., 8, 6063-6065.
    View publication on PubMed

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.212 additional information
-
 additional information steady-state enzyme kinetics, overview Rheum palmatum
2.3.1.212 0.01
-
 4-coumaroyl-CoA pH 8.0, 30°C, recombinant wild-type enzyme Rheum palmatum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.212 4-coumaroyl-CoA + malonyl-CoA + H2O Rheum palmatum
-
 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.212 Rheum palmatum Q94FV7
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.212 4-coumaroyl-CoA + malonyl-CoA + H2O
-
 Rheum palmatum 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
 ?
2.3.1.212 4-coumaroyl-CoA + malonyl-CoA + H2O one-step condensation Rheum palmatum 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
 ?
2.3.1.212 anthraniloyl-CoA + malonyl-CoA + H2O
-
 Rheum palmatum 4-hydroxy-1,3-dimethyl-2(1H)-quinolone + ?
-
 ?
2.3.1.212 anthraniloyl-CoA + methylmalonyl-CoA + H2O
-
 Rheum palmatum ?
-
 ?
2.3.1.212 additional information the enzyme reaction with the anthraniloyl-CoA proceeds without the decarboxylation step, and the amide formation immediately follows the condensation reactions of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) and malonyl-CoA (or methylmalonyl-CoA), mechanism, overview Rheum palmatum ?
-
 ?
2.3.1.212 N-methylanthraniloyl-CoA + 3 malonyl-CoA + H2O
-
 Rheum palmatum 1,3-dihydroxy-N-methylacridone + ?
-
 ?
2.3.1.212 N-methylanthraniloyl-CoA + methylmalonyl-CoA + H2O
-
 Rheum palmatum ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.212 bAS
-
 Rheum palmatum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.212 30
-
 assay at Rheum palmatum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.212 0.0298
-
 4-coumaroyl-CoA pH 8.0, 30°C, recombinant wild-type enzyme Rheum palmatum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.212 8 8.5
-
 Rheum palmatum

General Information

EC Number General Information Comment Organism
2.3.1.212 evolution the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily Rheum palmatum
2.3.1.212 physiological function benzalacetone synthase from Rheum palmatum efficiently catalyzes condensation of N-methylanthraniloyl-CoA (or anthraniloyl-CoA) with malonyl-CoA (or methylmalonyl-CoA) to produce 4-hydroxy-2(1H)-quinolones, a novel alkaloidal scaffold produced by a type III polyketide synthase, PKS. The quinolone alkaloids act as N-methyl-D-aspartate and serotonin 5-HT3 receptor antagonists. Moreover, they are also important intermediates in the chemical synthesis of alkaloids Rheum palmatum