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Literature summary for 2.3.1.212 extracted from

  • Abe, T.; Morita, H.; Noma, H.; Kohno, T.; Noguchi, H.; Abe, I.
    Structure function analysis of benzalacetone synthase from Rheum palmatum (2007), Bioorg. Med. Chem. Lett., 17, 3161-3166.
    View publication on PubMed
Search for more literature for 2.3.1.212

Cloned(Commentary)

Cloned (Comment) Organism
sequence comparison Rheum palmatum

Protein Variants

Protein Variants Comment Organism
C197G site-directed mutagenesis, the mutant shows an unaltered product pattern compared to the wild-type enzyme Rheum palmatum
C197T site-directed mutagenesis, the mutant shows an unaltered product pattern compared to the wild-type enzyme Rheum palmatum
G256L site-directed mutagenesis, the mutant shows 50% reduced activity but an unaltered product pattern compared to the wild-type enzyme Rheum palmatum
I214L/L215F site-directed mutagenesis, the mutant restores chalcone-forming activity Rheum palmatum
additional information formation of other products such as a tetraketide pyrone 4-coumaroyltriacetic acid lactone or naringenin chalcone is not detected for all the mutant enzymes Rheum palmatum
S338V site-directed mutagenesis, the mutant shows 2fold increased activity but an unaltered product pattern compared to the wild-type enzyme Rheum palmatum

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Rheum palmatum Q94FV7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-coumaroyl-CoA + malonyl-CoA + H2O
-
 Rheum palmatum 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
 ?
4-coumaroyl-CoA + malonyl-CoA + H2O a one-step decarboxylative condensation at pH 8.0 Rheum palmatum 2 CoA + 4-hydroxybenzalacetone + 2 CO2 i.e. 4-(4-hydroxyphenyl)but-3-en-2-one ?
4-coumaroylCoA + 2 malonyl-CoA + H2O wild-type and mutant BAS all afford the triketide pyrone bisnoryangonin after two condensations with malonyl-CoA at acidic pH 6.0 Rheum palmatum 2 CoA + bisnoryangonin + 2 CO2
-
 ?
additional information the wild-type enzyme also shows formation of benzalacetone, bisnoryangonin, and naringenin chalcone from 4-coumaroyl-CoA and malonyl-CoA as substrates, cf. EC 2.3.1.74, as well as formation of triacetic acid lactone, 5,7-dihydroxy-2-methylchromone, and 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-2-methyl-2,3-dihydro-4H-chromen-4-one (SEK4) and 2,7-dihydroxy-5-[(4-hydroxy-2-oxo-2H-pyran-6-yl)methyl]-5-methyl-2,3-dihydro-4H-chromen-4-one (SEK4b), from malonyl-CoA as a substrate, mechanisms, overview Rheum palmatum ?
-
 ?

Subunits

Subunits Comment Organism
More homology modeling, overview Rheum palmatum

Synonyms

Synonyms Comment Organism
bAS
-
 Rheum palmatum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
 maximum for bisnoryangonin formation activity Rheum palmatum
8
-
 maximum for benalacetone formation activity Rheum palmatum

General Information

General Information Comment Organism
evolution the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily Rheum palmatum
additional information pH-dependence of benzalacetone and bisnoryangonin production. Residues Ile214 and Leu215 are responsible for the diketide formation activity, unlike the case of CHS with residues L214 and F215, BAS utilizes an alternative pocket to lock the coumaroyl moiety for the diketide formation reaction, the second active-site Cys is not involved in the enzyme reaction,and Cys197 is not essential for the 4-hydroxybenzalacetone-producing activity, homology modeling Rheum palmatum