2.3.1.151: 2,3',4,6-tetrahydroxybenzophenone synthase
This is an abbreviated version!
For detailed information about 2,3',4,6-tetrahydroxybenzophenone synthase, go to the full flat file.
Word Map on EC 2.3.1.151
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2.3.1.151
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xanthones
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polyketide
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chalcone
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malonyl-coas
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hypericum
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synthases
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androsaemum
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benzoic
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4-coumaroyl-coa
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biphenyls
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starter
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mangostana
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perforatum
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cinnamic
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garcinia
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phytoalexins
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dibenzofurans
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rosaceae
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polyprenylated
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sorbus
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clusiaceae
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aucuparia
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centaurium
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triketide
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erythraea
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acid-specific
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ammonia-lyase
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maloideae
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pericarps
- 2.3.1.151
- xanthones
- polyketide
- chalcone
- malonyl-coas
-
hypericum
- synthases
- androsaemum
-
benzoic
- 4-coumaroyl-coa
- biphenyls
-
starter
- mangostana
- perforatum
-
cinnamic
-
garcinia
-
phytoalexins
- dibenzofurans
- rosaceae
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polyprenylated
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sorbus
- clusiaceae
- aucuparia
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centaurium
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triketide
- erythraea
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acid-specific
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ammonia-lyase
- maloideae
- pericarps
Reaction
3 Malonyl-CoA
+
Synonyms
2,3',4,6-Tetrahydroxybenzophenone synthase, benzophenone synthase, BPS, More, Synthase, benzophenone
ECTree
2.3.1.151 2,3',4,6-tetrahydroxybenzophenone synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.3.1.151 - 2,3',4,6-tetrahydroxybenzophenone synthase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 malonyl-CoA + 4-coumaroyl-CoA
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one + 2 CO2
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-
-
?
3 malonyl-CoA + acetyl-CoA
4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
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-
-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one + 4-hydroxy-6-phenyl-2H-pyran-2-one + 3 CO2
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the recombinant enzyme produces 2,4,6-trihydroxybenzophenone as the predominant product with benzoyl CoA as substrate but also lactones of tetraketide and triketide type
-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 6-phenyl-4-hydroxy-2-pyrone + 3 CO2
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relative activity: 100%, wildtype benzophenone synthase forms 2,4,6-trihydroxybenzophenone as a major product when incubated with benzoyl-CoA and malonyl-CoA, along with small amounts of 6-phenyl-4-hydroxy-2-pyrone
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-
?
3 malonyl-CoA + cinnamoyl-CoA
4 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 3 CO2
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-
-
?
3 malonyl-CoA + hexanoyl-CoA
4 CoA + 4-hydroxy-6-pentyl-2H-pyran-2-one + 5-hexanoyl-4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
-
-
-
?
3 malonyl-CoA + phenylacetyl-CoA
4 CoA + 4-hydroxy-6-(2-oxo-3-phenylpropyl)-2H-pyran-2-one + 6-benzyl-4-hydroxy-2H-pyran-2-one + 2-phenyl-1-(2,4,6-trihydroxyphenyl)ethanone + 3 CO2
-
-
-
?
3 malonyl-CoA + salicyl-CoA
4 CoA + 4-hydroxy-2H-chromen-2-one + 3 CO2
-
-
-
?
3-hydroxybenzoyl-CoA + 3 malonyl-CoA
2,3',4,6-tetrahydroxybenzophenone + 4 CoA + 3 CO2
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low activity, stepwise condensation
-
-
?
4 malonyl-CoA
4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
-
-
-
?
4-hydroxybenzoyl-CoA + 3 malonyl-CoA
2,4,4',6-trihydroxybenzophenone + 4 CoA + 3 CO2
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very low activity, stepwise condensation
-
-
?
Malonyl-CoA + 3-hydroxybenzoyl-CoA
?
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central step in xanthone biosynthesis
-
-
?
Malonyl-CoA + 4-hydroxybenzoyl-CoA
?
-
5% of the activity with benzoyl-CoA
-
-
?
N-methylanthraniloyl-CoA + malonyl-CoA
? + CoA + CO2
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low activity, stepwise condensation
-
-
?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 2,4,6-trihydroxybenzophenone + 2 CO2
-
44% of the activity with 3-hydroxybenzoyl-CoA
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?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 2,4,6-trihydroxybenzophenone + 2 CO2
-
-
-
?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 2,4,6-trihydroxybenzophenone + 2 CO2
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enzyme is inactive with CoA-linked cinnamic acids
-
-
?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 2,4,6-trihydroxybenzophenone + 2 CO2
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relative activity: 100%, wildtype benzophenone synthase forms 2,4,6-trihydroxybenzophenone as a major product when incubated with benzoyl-CoA and malonyl-CoA, along with small amounts of 6-phenyl-4-hydroxy-2-pyrone
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-
?
3 malonyl-CoA + 3-hydroxybenzoyl-CoA
4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2
-
-
-
?
3 malonyl-CoA + 3-hydroxybenzoyl-CoA
4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2
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3-hydroxybenzoyl-CoA is the preferred substrate
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-
?
3 malonyl-CoA + 3-hydroxybenzoyl-CoA
4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2
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49% of the activity with benzyol-CoA
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?
3 malonyl-CoA + 3-hydroxybenzoyl-CoA
4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2
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relative activity: 57%
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-
?
benzoyl-CoA + 3 malonyl-CoA
2,4,6-trihydroxybenzophenone + 4 CoA + 3 CO2
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stepwise condensation, polyketid synthesis, benzoic acid biosynthetic pathway overview, the 3'-hydroxylation is catalyzed by a cytochrome P450 monooxygenase in Hypericum androsaemum
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-
?
benzoyl-CoA + 3 malonyl-CoA
2,4,6-trihydroxybenzophenone + 4 CoA + 3 CO2
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preferred substrate, stepwise condensation
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-
?
additional information
?
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with acetyl CoA or malonyl CoA as a starter substrate, the enzyme only produces a triacetic lactone of triketide lactone type, with phenylacetyl-Coa also lactones of tetraketide and triketide type, and with hexanoyl-CoA phloroglucinol and triketide type lactones, substrate specificity, overview
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-
?
additional information
?
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-
with acetyl CoA or malonyl CoA as a starter substrate, the enzyme only produces a triacetic lactone of triketide lactone type, with phenylacetyl-Coa also lactones of tetraketide and triketide type, and with hexanoyl-CoA phloroglucinol and triketide type lactones, substrate specificity, overview
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-
?
additional information
?
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benzoyl-CoA is a minor starter molecule of polyketid synthesis for PKS in other plants, phylogenetic analysis
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-
?
additional information
?
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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
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-
?
