2.3.1.230: 2-heptyl-4(1H)-quinolone synthase
This is an abbreviated version!
For detailed information about 2-heptyl-4(1H)-quinolone synthase, go to the full flat file.
Word Map on EC 2.3.1.230
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2.3.1.230
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arachidonic
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20-hydroxyeicosatetraenoic
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omega-hydroxylase
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constrictor
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phenylephrine
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microcirculation
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cyp4a2
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clofibrate
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ppars
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lauric
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omega-hydroxylation
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interlobar
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20-hydroxyeicosa-6z,15z-dienoic
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myogenic
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n-methylsulfonyl-12,12-dibromododec-11-enamide
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proliferators
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nafenopin
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arterioles
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vasoconstrictor
- 2.3.1.230
-
arachidonic
-
20-hydroxyeicosatetraenoic
-
omega-hydroxylase
-
constrictor
- phenylephrine
-
microcirculation
- cyp4a2
- clofibrate
-
ppars
-
lauric
-
omega-hydroxylation
-
interlobar
-
20-hydroxyeicosa-6z,15z-dienoic
-
myogenic
- n-methylsulfonyl-12,12-dibromododec-11-enamide
-
proliferators
-
nafenopin
-
arterioles
-
vasoconstrictor
Reaction
Synonyms
2,4-dihydroxyquinoline synthase, PqsBC, PqsD, PsqD
ECTree
2.3.1.230 2-heptyl-4(1H)-quinolone synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 2.3.1.230 - 2-heptyl-4(1H)-quinolone 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-oxodecanoate + 2-aminobenzoyl-CoA
CoA + 2-heptyl-4(1H)-quinolone + CO2 + H2O
-
-
-
-
?
3-oxodecanoate + 2-aminobenzoyl-CoA
CoA + 2-heptyl-4-hydroxyquinoline + CO2 + H2O
-
-
-
-
?
3-oxodecanoyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 2-heptyl-3-hydroxy-4(1H)-quinolone + CO2
-
high concentrations and a longer incubation time is required in comparison to the free 3-oxodecanoic acid
-
-
?
3-oxodecanoyl-N-acetylcysteamine + 2-aminobenzoyl-CoA
N-acetylcysteamine + 2-heptyl-3-hydroxy-4(1H)-quinolone + CO2
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high concentrations and a longer incubation time is required in comparison to the free 3-oxodecanoic acid
-
-
?
3-oxohexanoate + 2-aminobenzoyl-CoA
CoA + 2-propyl-4(1H)-quinolone + CO2 + H2O
-
-
-
-
?
3-oxopentanoate + 2-aminobenzoyl-CoA
CoA + 2-ethyl-4(1H)-quinolone + CO2 + H2O
-
-
-
-
?
malonyl-[acyl-carrier protein] + 2-aminobenzoyl-CoA
CoA + acyl-carrier protein + 4-hydroxy-2(1H)-quinolone + CO2
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first, the 2-aminobenzoyl moiety is transferred to the active-site Cys of PqsD to form a 2-aminobenzoyl-PqsD intermediate, which then condenses with either malonyl-CoA or malonyl-acyl carrier protein to produce 3-(2-aminophenyl)-3-oxopropanoyl-CoA. This short-lived intermediate undergoes an intramolecular rearrangement to form 2,4-dihydroxyquinoline
i.e. 2,4-dihydroxyquinoline
-
?
additional information
?
-
-
no activity with malonic acid or 2-hydroxybenzoate
-
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
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2-aminobenzoyl-CoA i.e. anthraniloyl-CoA
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
2-aminobenzoyl-CoA i.e. anthraniloyl-CoA
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
2-aminobenzoyl-CoA i.e. anthraniloyl-CoA. PqsD is a key enzyme in the biosynthesis of the signal molecules 2-heptyl-4-hydroxyquinoline and 4-hydroxy-2(1H)-quinolone, that are involved in regulation of virulence factor production and biofilm formation
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
2-aminobenzoyl-CoA i.e. anthraniloyl-CoA. The enzyme is involved in the biosynthesis of the Pseudomonas Quinolone Signal
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
the enzyme is involved in the biosynthesis of 2,4-dihydroxyquinoline. Pseudomonas aeruginosa is a Gram-negative opportunistic pathogen that is a highly interactive organism secreting a variety of chemical signals. One intercellular signaling system unique to Pseudomonas and Burkholderia species is the production of hydrophobic quinolines. These quinoline derivatives are 4-hydroxy-2-heptylquinoline, 3,4-dihydroxy-2-heptylquinoline, and 2,4-dihydroxyquinoline
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
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the enzyme is involved in the biosynthesis of the signal molecules 2-heptyl-3-hydroxy-4(1H)-quinolone and 4-hydroxy-2(1H)-quinolone. These compounds are part of the quorum-sensing systems that is based on the production and release of small signaling molecules, called autoinducers, that increase in concentration as a function of cell density and activate corresponding transcriptional regulators after a threshold concentration has been reached
-
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
2-aminobenzoyl-CoA i.e. anthraniloyl-CoA. Ping-pong mechanism for PqsD with 2-aminobenzoyl-CoA as first substrate. Trajectory analysis of different PqsD complexes evidences ligand-dependent induced-fit motions affecting the modified 2-aminobenzoyl-CoA funnel access to the exposure of a secondary channel. A tunnel-network is formed in which Ser317 plays an important role by binding to both substrates
i.e. 2,4-dihydroxyquinoline
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
catalyzes the decarboxylative Claisen condensation with malonyl-CoA.
-
-
?
malonyl-CoA + 2-aminobenzoyl-CoA
2 CoA + 4-hydroxy-2(1H)-quinolone + CO2
-
first, the 2-aminobenzoyl moiety is transferred to the active-site Cys of PqsD to form a 2-aminobenzoyl-PqsD intermediate, which then condenses with either malonyl-CoA or malonyl-acyl carrier protein to produce 3-(2-aminophenyl)-3-oxopropanoyl-CoA. This short-lived intermediate undergoes an intramolecular rearrangement to form 2,4-dihydroxyquinoline
i.e. 2,4-dihydroxyquinoline
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X2; Q9I4X1
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X2; Q9I4X1
-
-
-
?
