2.3.1.212: benzalacetone synthase
This is an abbreviated version!
For detailed information about benzalacetone synthase, go to the full flat file.
Word Map on EC 2.3.1.212
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2.3.1.212
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polyketide
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chalcone
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palmatum
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rheum
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plant-specific
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raspberry
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diketide
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phenylbutanoids
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flavor
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unnatural
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p-coumaric
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4-coumarate
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synthesis
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stilbene
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phenylpropanoids
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crispum
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idaeus
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methylmalonyl-coa
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cuspidatum
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condensations
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naringenin
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arachis
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polygonum
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petroselinum
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baicalensis
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fragrance
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rhubarb
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scutellaria
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tetraketide
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quinolone
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rubus
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p-coumaroyl-coa
- 2.3.1.212
- polyketide
- chalcone
- palmatum
- rheum
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plant-specific
- raspberry
-
diketide
-
phenylbutanoids
-
flavor
-
unnatural
-
p-coumaric
- 4-coumarate
- synthesis
- stilbene
-
phenylpropanoids
- crispum
- idaeus
- methylmalonyl-coa
- cuspidatum
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condensations
- naringenin
- arachis
-
polygonum
-
petroselinum
- baicalensis
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fragrance
- rhubarb
-
scutellaria
-
tetraketide
-
quinolone
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rubus
- p-coumaroyl-coa
Reaction
Synonyms
bAS, HsPKS3, PKS1, RinPKS1, RiPKS4, RpBAS
ECTree
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General Information
General Information on EC 2.3.1.212 - benzalacetone synthase
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evolution
physiological function
additional information
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the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily
evolution
the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily
evolution
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the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily
evolution
the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily
evolution
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the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily
evolution
the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily, amino acids C164, F215, H303 and N336 are conserved
evolution
the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily. BAS lacks the critical residue Phe215, that is important in the polyketide formation reactions, structure-function relationship of the plant type III PKSs, overview. The absence of Phe215 in BAS accounts for the interruption of the polyketide chain elongation at the diketide stage
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
evolution
the enzyme is a plant-specific type III polyketide synthase of the chalcone synthase (CHS) superfamily. Members of the CHS-superfamily enzymes do not form a species-specific cluster, but instead group into subfamilies according to their enzymatic function. BAS lacks the active-site Phe215 residue (numbering in CHS), which has been proposed to help orient substrates and intermediates during the sequential condensation of 4-coumaroyl-CoA with malonyl-CoA in CHS, while the catalytic cysteine-histidine dyad (Cys164-His303) in CHS is well conserved in BAS
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4-hydroxybenzalacetone, i.e. 4-hydroxyphenylbutan-2-one, the characteristic aroma compound of raspberries, is synthesized from 4-coumaryl-CoA and malonyl-CoA in a two-step reaction sequence that is catalyzed by benzalacetone synthase and benzalacetone reductase. 4-Hydroxybenzalacetone inhibits mycelial growth of the raspberry pathogen Phytophthora fragariae var. rub
physiological function
BAS plays a crucial role in the biosynthesis of pharmaceutically important phenylbutanone glucoside, lindleyin, the active principle of the anti-inflammatory action of the medicinal plant, and it plays a crucial role for the construction of the C6-C4 moiety of a variety of natural products such as medicinally important gingerols in ginger plant
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
physiological function
pBAS catalyzes the one-step, decarboxylative condensation of 4-coumaroyl-CoA with malonyl-CoA to produce the C6-C4 benzalacetone scaffold
physiological function
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the enzyme is a polyketide synthase, PKS, involved in the raspberry flavor and color polyketide-derivatives biosynthetic pathway, developmental regulation of PKS during fruit ripening, overview
physiological function
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4-hydroxybenzalacetone, i.e. 4-hydroxyphenylbutan-2-one, the characteristic aroma compound of raspberries, is synthesized from 4-coumaryl-CoA and malonyl-CoA in a two-step reaction sequence that is catalyzed by benzalacetone synthase and benzalacetone reductase. 4-Hydroxybenzalacetone inhibits mycelial growth of the raspberry pathogen Phytophthora fragariae var. rub
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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
additional information
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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
additional information
structure-function relationship, homology modeling, overview
additional information
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structure-function relationship, homology modeling, overview
additional information
the absence of Phe215 in BAS accounts for the interruption of the polyketide chain elongation at the diketide stage compared to chalcone synthase, EC 2.3.1.74, structure-function relationship , overview. BAS catalytic residues are Asn336, His303, and Cys164, active site structure, overview
additional information
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the absence of Phe215 in BAS accounts for the interruption of the polyketide chain elongation at the diketide stage compared to chalcone synthase, EC 2.3.1.74, structure-function relationship , overview. BAS catalytic residues are Asn336, His303, and Cys164, active site structure, overview