2.3.1.208: 4-hydroxycoumarin synthase
This is an abbreviated version!
For detailed information about 4-hydroxycoumarin synthase, go to the full flat file.
Reaction
Synonyms
biphenyl synthase, BIS, BIS1, BIS2, BIS3, More
ECTree
2.3.1.208 4-hydroxycoumarin synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.3.1.208 - 4-hydroxycoumarin synthase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
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
malonyl-CoA + 3-hydroxybenzoyl-CoA
2 CoA + 2-oxabicyclo[4.3.1]deca-1(10),6,8-triene-3,5-dione + CO2
-
-
-
?
malonyl-CoA + 2-hydroxybenzoyl-CoA
2 CoA + 4-hydroxycoumarin + CO2
-
-
-
-
?
malonyl-CoA + 2-hydroxybenzoyl-CoA
2 CoA + 4-hydroxycoumarin + CO2
-
-
-
?
malonyl-CoA + 2-hydroxybenzoyl-CoA
2 CoA + 4-hydroxycoumarin + CO2
-
-
-
-
?
malonyl-CoA + 2-hydroxybenzoyl-CoA
2 CoA + 4-hydroxycoumarin + CO2
-
i.e. salicyl-CoA, reaction via an intermediate diketide
-
-
?
additional information
?
-
-
for the bifunctional BIS, the preferred starter substrates are benzoyl-CoA and salicoyl-CoA, leading to the formation of 3,5-dihydroxybiphenyl and 4-hydroxycoumarin, EC 2.3.1.177 and 2.3.1.208, respectively, in the presence of malonyl-CoA as extender molecule
-
-
?
additional information
?
-
-
bifunctional enzyme, biphenyl synthase, BIS, catalyzes the formation of a linear tetraketide intermediate from benzoyl-CoA and three molecules of malonyl-CoA but uses an alternative intramolecular cyclization reaction to form 3,5-dihydroxybiphenyl, EC 2.3.1.177. When incubated with 2-hydroxybenzoyl (salicyl)-CoA, BIS catalyzes a single decarboxylative condensation with malonyl-CoA to form 4-hydroxycoumarin, EC 2.3.1.208
-
-
?
additional information
?
-
-
biphenyl synthase isozyme BIS1, in contrast to isozymes BIS2 and BIS3, does not prefer 2-hydroxybenzoyl (salicyl)-CoA as a starter substrat, but also catalyzes a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
biphenyl synthase isozyme BIS1, in contrast to isozymes BIS2 and BIS3, does not prefer 2-hydroxybenzoyl (salicyl)-CoA as a starter substrat, but also catalyzes a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
biphenyl synthase isozyme BIS1, in contrast to isozymes BIS2 and BIS3, does not prefer 2-hydroxybenzoyl (salicyl)-CoA as a starter substrat, but also catalyzes a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
-
for the bifunctional BIS, the preferred starter substrates are benzoyl-CoA and salicoyl-CoA, leading to the formation of 3,5-dihydroxybiphenyl and 4-hydroxycoumarin, EC 2.3.1.177 and 2.3.1.208, respectively, in the presence of malonyl-CoA as extender molecule
-
-
?
additional information
?
-
-
in contrast to isozyme BIS1, biphenyl synthase isoenzymes BIS2 and BIS3 prefer ortho-hydroxybenzoyl (salicyl)-CoA as a starter substrate and catalyze a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
in contrast to isozyme BIS1, biphenyl synthase isoenzymes BIS2 and BIS3 prefer ortho-hydroxybenzoyl (salicyl)-CoA as a starter substrate and catalyze a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
in contrast to isozyme BIS1, biphenyl synthase isoenzymes BIS2 and BIS3 prefer ortho-hydroxybenzoyl (salicyl)-CoA as a starter substrate and catalyze a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin
-
-
?
additional information
?
-
-
substrate specificities of BIS isoenzymes from cell cultures, overview. The bifunctional enzyme also forms 3,5-dihydroxybiphenyl from malonyl-CoA and benzoyl-CoA, reaction of biphenyl synthase, EC 2.3.1.177. When benzoyl-CoA is replaced with salicyl-CoA as a starter substrate, the enzyme catalyzes a single decarboxylative condensation reaction with malonyl-CoA to form a diketide intermediate which undergoes intramolecular cyclization by nucleophilic attack of the phenol group on the CoA- or cysteine-tethered C-1 thioester, yielding 4-hydroxycoumarin after enolization. No activity with 4-hydroxybenzoyl-CoA, cinnamoyl-CoA, 2-coumaroyl-CoA, 3-coumaroyl-CoA, 4-coumaroyl-CoA, and acetyl-CoA or with free salicylic acid or 2-coumaric acid
-
-
?
additional information
?
-
substrate specificities of BIS isoenzymes from cell cultures, overview. The bifunctional enzyme also forms 3,5-dihydroxybiphenyl from malonyl-CoA and benzoyl-CoA, reaction of biphenyl synthase, EC 2.3.1.177. When benzoyl-CoA is replaced with salicyl-CoA as a starter substrate, the enzyme catalyzes a single decarboxylative condensation reaction with malonyl-CoA to form a diketide intermediate which undergoes intramolecular cyclization by nucleophilic attack of the phenol group on the CoA- or cysteine-tethered C-1 thioester, yielding 4-hydroxycoumarin after enolization. No activity with 4-hydroxybenzoyl-CoA, cinnamoyl-CoA, 2-coumaroyl-CoA, 3-coumaroyl-CoA, 4-coumaroyl-CoA, and acetyl-CoA or with free salicylic acid or 2-coumaric acid
-
-
?
additional information
?
-
substrate specificities of BIS isoenzymes from cell cultures, overview. The bifunctional enzyme also forms 3,5-dihydroxybiphenyl from malonyl-CoA and benzoyl-CoA, reaction of biphenyl synthase, EC 2.3.1.177. When benzoyl-CoA is replaced with salicyl-CoA as a starter substrate, the enzyme catalyzes a single decarboxylative condensation reaction with malonyl-CoA to form a diketide intermediate which undergoes intramolecular cyclization by nucleophilic attack of the phenol group on the CoA- or cysteine-tethered C-1 thioester, yielding 4-hydroxycoumarin after enolization. No activity with 4-hydroxybenzoyl-CoA, cinnamoyl-CoA, 2-coumaroyl-CoA, 3-coumaroyl-CoA, 4-coumaroyl-CoA, and acetyl-CoA or with free salicylic acid or 2-coumaric acid
-
-
?
additional information
?
-
-
two molecules of 4-hydroxycoumarin spontaneously combine with formaldehyde to give dicoumarol
-
-
?
