2.3.1.220: 2,4,6-trihydroxybenzophenone synthase
This is an abbreviated version!
For detailed information about 2,4,6-trihydroxybenzophenone synthase, go to the full flat file.
Word Map on EC 2.3.1.220
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2.3.1.220
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falciparum
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plasmodium
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merozoite
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malaria
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subunit-based
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erythrocyte
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aotus
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high-activity
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receptor-ligand
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sporozoite
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anti-malarial
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multi-stage
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protection-inducing
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multiepitope
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hyaluronan
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enzyme-treated
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multi-antigenic
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hyaluronan-binding
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rhoptries
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microneme
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chemically-synthesized
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rhoptry-associated
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parasitophorous
- 2.3.1.220
- falciparum
- plasmodium
-
merozoite
- malaria
-
subunit-based
- erythrocyte
- aotus
-
high-activity
-
receptor-ligand
-
sporozoite
-
anti-malarial
-
multi-stage
-
protection-inducing
-
multiepitope
- hyaluronan
-
enzyme-treated
-
multi-antigenic
-
hyaluronan-binding
-
rhoptries
-
microneme
-
chemically-synthesized
-
rhoptry-associated
-
parasitophorous
Reaction
3 malonyl-CoA
+
Synonyms
benzophenone synthase, BPS, HaBPS
ECTree
2.3.1.220 2,4,6-trihydroxybenzophenone synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.3.1.220 - 2,4,6-trihydroxybenzophenone 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
3 malonyl-CoA + 3-hydroxybenzoyl-CoA
4 CoA + 2,3',4,6-tetrahydroxybenzophenone + 3 CO2
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43.5% of the activity compared to benzoyl-CoA
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-
?
3 malonyl-CoA + butyryl-CoA
4 CoA + 2,4,6-trihydroxybutyrophenone + 6-propyl-4-hydroxy-2-pyrone + 3 CO2
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formation of 36.8% 2,4,6-trihydroxybutyrophenone and 6-propyl-4-hydroxy-2-pyrone as side product
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-
?
3 malonyl-CoA + hexanoyl-CoA
4 CoA + 4-hydroxy-6-pentyl-2H-pyran-2-one + 4-hydroxy-6-(2-oxoheptyl)-2H-pyran-2-one + 3 CO2
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-
-
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?
3 malonyl-CoA + isobutyryl-CoA
4 CoA + 2,4,6-trihydroxyisobutyrophenone + 3 CO2
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formation of 46.4% 2,4,6-trihydroxyisobutyrophenone and 34.2% 6-isopropyl-4-hydroxy-2-pyrone as side product
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-
?
3 malonyl-CoA + isobutyryl-CoA
4 CoA + phloroisobutyrophenone + 3 CO2
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-
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?
3 malonyl-CoA + isovaleryl-CoA
4 CoA + phloroisovalerophenone + 3 CO2
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-
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?
3 malonyl-CoA + phenylacetyl-CoA
4 CoA + 2,4,6-trihydroxyphenylbenzylketone + 3 CO2
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-
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-
?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 6-phenyl-4-hydroxy-2-pyrone + 2 CO2
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reaction of mutant T135L, no activity with the wild-type enzyme. The T135L mutant adds only two acetyl groups to the benzoyl starter unit to form a triketide intermediate which then cyclized into 6-phenyl-4-hydroxy-2-pyrone via C5 keto-enol oxygen -> C1 lactonization
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-
?
2 malonyl-CoA + benzoyl-CoA
3 CoA + 6-phenyl-4-hydroxy-2-pyrone + 2 CO2
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reaction of mutant T135L, no activity with the wild-type enzyme. The T135L mutant adds only two acetyl groups to the benzoyl starter unit to form a triketide intermediate which then cyclized into 6-phenyl-4-hydroxy-2-pyrone via C5 keto-enol oxygen -> C1 lactonization
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-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
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?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
a minor amount of tetraketide lactone and triketide lactone are also obtained
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-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
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-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
-
-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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benzoyl-CoA is the preferred starter substrate of the wild-type enzyme, activity by wild-type enzyme and mutant T135L
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-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
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-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
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?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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-
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?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
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benzoyl-CoA is the preferred starter substrate of the wild-type enzyme, very low 2,4,6-trihydroxybenzophenone-forming activity with the mutant T135L
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-
?
additional information
?
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the recombinant enzyme produces 2,4,6-trihydroxybenzophenone as the predominant product with benzoyl CoA as substrate. It also accepts other substrates, such as other plant PKSs, and used 1-3 molecules of malonyl CoA to form various phloroglucinol-type and polyketide lactone-type compounds
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?
additional information
?
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3-hydroxybenzoyl-CoA is the second best starter substrate for the wild-type enzyme but a poor starter molecule for the mutant enzyme T135L, resulting in formation of 2,3',4,6-tetrahydroxybenzophenone, reaction of EC 2.3.1.151. Product identification by mass spectrometry. No activity by wild-type enzyme and mutant T135L with 2-hydroxybenzoyl-CoA, 4-hydroxybenzoyl-CoA, cinnamoyl-CoA, 2-coumaroyl-CoA, 3-coumaroyl-CoA, 4-coumaroyl-CoA, and acetyl-CoA
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-
?
additional information
?
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the enzyme does not accept 2-hydroxybenzoyl-CoA and 4-hydroxybenzoyl-CoA, acetyl-CoA, and CoA esters of cinnamic acids
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additional information
?
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chalcone synthase, CHS EC 2.3.1.74, shows broad substrate specificity, overview. Both aromatic and aliphatic CoA esters are accepted in the active site of the enzyme as a starter substrate for the complex condensation reaction. CHS converts benzoyl-CoA to phlorobenzophenone, i.e. 2,4,6-trihydroxybenzophenone, along with pyrone by-products, and it converts phenylacetyl-CoA to an unnatural aromatic polyketide, phlorobenzylketone, i.e. 2,4,6-trihydroxyphenylbenzylketone. Scutellaria baicalensis CHS also accepts aliphatic CoA esters, isovaleryl-CoA and isobutyryl-CoA, to produce phloroacylphenones. Hexanoyl-CoA only affords pyrone derivatives without formation of a new aromatic ring
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?
additional information
?
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3-hydroxybenzoyl-CoA is the second best starter substrate for the wild-type enzyme but a poor starter molecule for the mutant enzyme T135L, resulting in formation of 2,3',4,6-tetrahydroxybenzophenone, reaction of EC 2.3.1.151. The benzoyl-primed triketides are covalently attached to the catalytic Cys167. The wild-type enzyme catalyzes another acetyl addition to the intermediate triketide
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?
