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Literature summary extracted from

  • Shimokawa, Y.; Morita, H.; Abe, I.
    Structure-based engineering of benzalacetone synthase (2010), Bioorg. Med. Chem. Lett., 20, 5099-5103.
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
2.3.1.212 L132A site-directed mutagenesis, the substitution expands the product chain length to produce 4-coumaroyltriacetic acid lactone after three condensations with malonyl-CoA, but without the formation of the aromatic ring system Rheum palmatum
2.3.1.212 L132C site-directed mutagenesis, the substitution expands the product chain length to produce 4-coumaroyltriacetic acid lactone after three condensations with malonyl-CoA, but without the formation of the aromatic ring system Rheum palmatum
2.3.1.212 L132F site-directed mutagenesis, replacement of Leu132 with bulky aromatic residues, Phe, Tyr and Trp, causes a 1.2fold increase in the benzalacetone-forming activity at pH 8.0, whereas the bisnoryangonin-forming activity is retained or significantly decreased at pH 6.5 Rheum palmatum
2.3.1.212 L132G site-directed mutagenesis, no altered activity compared to the wild-type enzyme Rheum palmatum
2.3.1.212 L132P site-directed mutagenesis, the L132P mutant exhibits drastically decreased benzalacetone- and bisnoryangonin-forming activities Rheum palmatum
2.3.1.212 L132S site-directed mutagenesis, the substitution expands the product chain length to produce 4-coumaroyltriacetic acid lactone after three condensations with malonyl-CoA, but without the formation of the aromatic ring system Rheum palmatum
2.3.1.212 L132T site-directed mutagenesis, the chalcone-forming L132T mutant shows broad substrate specificity. It accepts benzoyl-CoA as the starter substrate to produce a trace amount of 2,4,6-trihydroxybenzophenone, after condensations of benzoyl-CoA with three molecules of malonyl-CoA, along with benzoate-primed triketide and tetraketide pyrones as major products Rheum palmatum
2.3.1.212 L132T/I214L/L215F site-directed mutagenesis, the triple mutation does not improve the chalcone-forming activity, but instead results in a significant loss of activity Rheum palmatum
2.3.1.212 L132W site-directed mutagenesis, replacement of Leu132 with bulky aromatic residues, Phe, Tyr and Trp, blocks the entrance of the coumaroyl binding pocket and causes a 1.2fold increase in the benzalacetone-forming activity at pH 8.0, whereas the bisnoryangonin-forming activity is retained or significantly decreased at pH 6.5 Rheum palmatum
2.3.1.212 L132Y site-directed mutagenesis, replacement of Leu132 with bulky aromatic residues, Phe, Tyr and Trp, causes a 1.2fold increase in the benzalacetone-forming activity at pH 8.0, whereas the bisnoryangonin-forming activity is retained or significantly decreased at pH 6.5 Rheum palmatum
2.3.1.212 additional information the single amino acid substitution L132T restores the chalcone-forming activity of chalcone synthase, EC 2.3.1.74, in BAS, probably due to restoration of the coumaroyl binding pocket in the active-site cavity, whereas the Ala, Ser, and Cys substitutions expand the product chain length to produce 4-coumaroyltriacetic acid lactone after three condensations with malonyl-CoA, but without the formation of the aromatic ring system Rheum palmatum

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 kinetics analysis for benzalacetone-, bisnoryangonin-, and chalcone-forming activities, overview 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 BAS catalyzes the decarboxylative coupling of 4-coumaroyl-CoA with malonyl-CoA to produce the diketide benzalacetone Rheum palmatum 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
 ?
2.3.1.212 4-coumaroylCoA + 2 malonyl-CoA + H2O
-
 Rheum palmatum 2 CoA + bisnoryangonin + 2 CO2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.212 bAS
-
 Rheum palmatum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.212 8
-
 the reaction is highly pH-dependent 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. Comparison of the primary sequences and and secondary structures of BAS and other type III PKSs, overview Rheum palmatum
2.3.1.212 additional information structure-function relationship, homology modeling, overview Rheum palmatum