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Information on EC 2.3.1.B38 - heptylquinolone synthase
for references in articles please use BRENDA:EC2.3.1.B38preliminary BRENDA-supplied EC number
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2.3.1.B38 heptylquinolone synthaseSpecify your search results
Word Map
- 2.3.1.B38
- aeruginosa
-
opportunistic
-
condensing
- n-oxides
-
2-heptyl-3-hydroxy-41h-quinolone
-
heterodimeric
The expected taxonomic range for this enzyme is: Pseudomonas aeruginosa
Reaction Schemes
Synonyms
2-heptyl-4(1H)-quinolone synthase, PqsB, PqsBC, PqsC, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-heptyl-4(1H)-quinolone synthase
PqsB
PqsBC
PqsC
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
octanoyl-CoA + 2-aminobenzoylacetate = 2-heptylquinolin-4(1H)-one + CO2 + H2O
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-
-
-
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SYSTEMATIC NAME
IUBMB Comments
octanoyl-CoA:2-aminobenzoylacetate octanoyltransferase |cyclising||
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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
octanoyl-CoA + 2-aminobenzoylacetate
CoA + 2-heptylquinolin-4(1H)-one + CO2 + H2O
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product is a signal molecule in Pseudomonas aeruginosa. The initial product is 1-(2-aminophenyl)decane-1,3-dione which spontaneously rearranges to the product under the elimination of water
-
?
additional information
?
-
the catalytic His269 residue is not involved in acyl-enzyme formation, but contributes to an acylation-dependent increase in affinity for the second substrate 2-aminobenzoylacetate. Octanoylation of Cys129 of PqsC is independent of His269
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
octanoyl-CoA + 2-aminobenzoylacetate
CoA + 2-heptylquinolin-4(1H)-one + CO2 + H2O
-
product is a signal molecule in Pseudomonas aeruginosa. The initial product is 1-(2-aminophenyl)decane-1,3-dione which spontaneously rearranges to the product under the elimination of water
-
?
additional information
?
-
the catalytic His269 residue is not involved in acyl-enzyme formation, but contributes to an acylation-dependent increase in affinity for the second substrate 2-aminobenzoylacetate. Octanoylation of Cys129 of PqsC is independent of His269
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
octanoyl-CoA + (2-aminobenzoyl)acetate
2-heptyl-4-quinolone + CoA + CO2 + H2O
Q9I4X1; Q9I4X2
-
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(furan-3-yl)(2-nitrophenyl)methanol
Q9I4X1; Q9I4X2
PqsBC inhibitor reduces the production of the MvfR natural ligands in wild-type strain PA14 down to 34% at its highest concentration
2-aminoacetophenone
pathway-inherent competitive inhibitor. EC50 of 46 microM in the in vitro assay
ethyl 3-benzyl-1-[2-(4-fluoroanilino)-2-oxoethyl]-2,4-dioxo-1,3,4,5,6,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(2H)-carboxylate
Q9I4X1; Q9I4X2
PqsBC inhibitor reduces the production of the MvfR natural ligands in wild-type strain PA14 down to 35% at its highest concentration
additional information
2-heptyl-4(1H)-quinolone and 2-heptyl-3-hydroxy-4(1H)-quinolone as well as ,4-dihydroxyquinoline at concentrations up to 50 microM do not affect PqsBC activity
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additional information
Q9I4X1; Q9I4X2
Pseudomonas aeruginosa is a Gram-negative bacterium, which causes opportunistic infections in immuno-compromised individuals. Due to its multiple resistances toward antibiotics, the development of new drugs is required. Interfering with quorum sensing (QS), a cell-to-cell communication system, has shown to be highly efficient in reducing Pseudomonas aeruginosa pathogenicity. One of its QS systems employs Pseudomonas quinolone signal (PQS) and 4-hydroxy-2-heptylquinoline (HHQ) as signal molecules. Both activate the transcriptional regulator MvfR (Multiple Virulence Factor Regulator), also called PqsR, driving the production of QS molecules as well as toxins and biofilm formation. Effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO). The employed synthetic MvfR antagonist fully inhibits pqs small molecule formation showing expected sigmoidal dose-response curves for 2-AA, HQNO, HHQ, and PQS
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.105
2-aminobenzoylacetate
pH 8.2, temperature not specified in the publication
0.006
octanoyl-CoA
pH 8.2, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6.8
octanoyl-CoA
pH 8.2, temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.054 - 0.056
2-aminoacetophenone
pH 8.2, temperature not specified in the publication
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
A0A0H2Z7A3 i.e. subunit PqsC, and A0A0H2Z7K6, i.e. subunit PqsB
A0A0H2Z7A3; A0A0H2Z7K6
UniProt
brenda
A0A0H2Z7A3 i.e. subunit PqsC, and A0A0H2Z7K6, i.e. subunit PqsB
A0A0H2Z7A3; A0A0H2Z7K6
UniProt
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
Q9I4X1; Q9I4X2
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
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malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
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malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
-
malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
-
malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
-
malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
-
malfunction
-
effects of QS inhibitors (QSIs), such as MvfR antagonists and PqsBC inhibitors, on the biosynthesis of the MvfR-regulated small molecules 2'-aminoacetophenone (2-AA), dihydroxyquinoline (DHQ), 4-hydroxy-2-heptylquinoline (HHQ), Pseudomonas quinolone signal (PQS), and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO)
-
metabolism
Q9I4X1; Q9I4X2
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
metabolism
-
the 2-heptyl-4(1H)-quinolone synthase is involved in the biosynthetic pathway of MvfR-related small molecules. In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after quorum sensing inhibitor treatment
-
physiological function
A0A0H2Z7A3; A0A0H2Z7K6
4-hydroxy-2-alkylquinoline biosynthesis, which requires the PqsABCD enzymes, proceeds by a two-step pathway: PqsD mediates the synthesis of 2-aminobenzoylacetate from anthraniloyl-coenzyme A and malonyl-coenzyme A, then the decarboxylating coupling of 2-aminobenzoylacetate to an octanoate group linked to PqsC produces 4-hydroxy-2-heptylquinoline, the direct precursor of 3,4-dihydroxy-2-heptylquinoline. PqsB is tightly associated with PqsC and required for the second step. None of the pqsA-, pqsB-, pqsC-, and pqs- mutants produces measurable amounts of 4-hydroxy-2-alkylquinolines, and PqsB and PqsC have to be present simultaneously to transform the intermediate into 4-hydroxy-2-heptylquinoline
physiological function
-
4-hydroxy-2-alkylquinoline biosynthesis, which requires the PqsABCD enzymes, proceeds by a two-step pathway: PqsD mediates the synthesis of 2-aminobenzoylacetate from anthraniloyl-coenzyme A and malonyl-coenzyme A, then the decarboxylating coupling of 2-aminobenzoylacetate to an octanoate group linked to PqsC produces 4-hydroxy-2-heptylquinoline, the direct precursor of 3,4-dihydroxy-2-heptylquinoline. PqsB is tightly associated with PqsC and required for the second step. None of the pqsA-, pqsB-, pqsC-, and pqs- mutants produces measurable amounts of 4-hydroxy-2-alkylquinolines, and PqsB and PqsC have to be present simultaneously to transform the intermediate into 4-hydroxy-2-heptylquinoline
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). PQSC_PSEAE
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
348
0
38239
Swiss-Prot
-
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
mutant C129A, to 2 A resolution, space group P212121. The heterodimer displays a pseudo 2fold symmetry. Subunit PqsC has an active site comprised of Cys129 and His269
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
V299N
substitution leads to significant activity toward the deamino substrate analog benzoylacetate, suggesting that the substrate 2-aminobenzoylacetate itself supplies the asparagine-equivalent amino function that assists in catalysis
additional information
additional information
Q9I4X1; Q9I4X2
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
additional information
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Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
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additional information
-
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
additional information
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Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
additional information
-
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
additional information
-
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
additional information
-
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
additional information
-
Pseudomonas aeruginosa strain PA14 isogenic transposon pqsC mutant
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Dulcey, C.E.; Dekimpe, V.; Fauvelle, D.A.; Milot, S.; Groleau, M.C.; Doucet, N.; Rahme, L.G.; Lepine, F.; Deziel, E.
The end of an old hypothesis: the Pseudomonas signaling molecules 4-hydroxy-2-alkylquinolines derive from fatty acids, not 3-ketofatty acids
Chem. Biol.
20
1481-1491
2013
Pseudomonas aeruginosa (A0A0H2Z7A3 and A0A0H2Z7K6), Pseudomonas aeruginosa UCBPP-PA14 (A0A0H2Z7A3 and A0A0H2Z7K6)
brenda
Drees, S.L.; Li, C.; Prasetya, F.; Saleem, M.; Dreveny, I.; Williams, P.; Hennecke, U.; Emsley, J.; Fetzner, S.
PqsBC, a condensing enzyme in the biosynthesis of the Pseudomonas aeruginosa quinolone signal: crystal structure, inhibition, and reaction mechanism
J. Biol. Chem.
291
6610-6624
2016
Pseudomonas aeruginosa (Q9I4X1)
brenda
Allegretta, G.; Maurer, C.; Eberhard, J.; Maura, D.; Hartmann, R.; Rahme, L.; Empting, M.
In-depth profiling of MvfR-regulated small molecules in Pseudomonas aeruginosa after Quorum Sensing inhibitor treatment
Front. Microbiol.
8
924
2017
Pseudomonas aeruginosa (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa ATCC 15692 (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa 1C (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa PRS 101 (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa DSM 22644 (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa CIP 104116 (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa LMG 12228 (Q9I4X1 AND Q9I4X2), Pseudomonas aeruginosa JCM 14847 (Q9I4X1 AND Q9I4X2)
brenda
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