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Information on EC 1.14.13.182 - 2-heptyl-3-hydroxy-4(1H)-quinolone synthase and Organism(s) Pseudomonas aeruginosa and UniProt Accession Q9I0Q0

for references in articles please use BRENDA:EC1.14.13.182
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IUBMB Comments
The enzyme from the bacterium Pseudomonas aeruginosa catalyses the terminal step in biosynthesis of the signal molecule 2-heptyl-3,4-dihydroxyquinoline that plays a role in regulation of virulence genes.
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Pseudomonas aeruginosa
UNIPROT: Q9I0Q0
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The taxonomic range for the selected organisms is: Pseudomonas aeruginosa
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
2-heptyl-3,4-dihydroxyquinoline synthase, Aqm, PqsH, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2-heptyl-3,4-dihydroxyquinoline synthase
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SYSTEMATIC NAME
IUBMB Comments
2-heptyl-4(1H)-quinolone,NADH:oxygen oxidoreductase (3-hydroxylating)
The enzyme from the bacterium Pseudomonas aeruginosa catalyses the terminal step in biosynthesis of the signal molecule 2-heptyl-3,4-dihydroxyquinoline that plays a role in regulation of virulence genes.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-heptyl-1-hydroxyquinolin-4(1H)-one one + NADH + H+ + O2
2-heptyl-1,3-dihydroxy-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
-
-
-
?
2-heptyl-4(1H)-quinolone + NADH + H+ + O2
2-heptyl-3-hydroxy-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
2-heptyl-4(1H)-quinolone + NADPH + H+ + O2
2-heptyl-3-hydroxy-4(1H)-quinolone + NADP+ + H2O
show the reaction diagram
kcat/KM for NADH is 20fold higher than kcat/Km for NADPH
-
-
?
2-heptylquinolin-4(1H)-one + NADH + H+ + O2
2-heptyl-3-hydroxy-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
2-heptylquinolin-4(1H)-one and 2-nonylquinolin-4(1H)-one, preferred substrates
-
-
?
2-nonyl-4(1H)-quinolone + NADH + H+ + O2
3-hydroxy-2-nonyl-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
the alkyl side chain of 2-heptyl-4-quinolone is critical for PqsH activity with the highest activity observed for alkyl chain lengths of 7 and 9 carbons
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-
?
2-nonylquinolin-4(1H)-one + NADH + H+ + O2
3-hydroxy-2-nonyl-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
2-heptylquinolin-4(1H)-one and 2-nonylquinolin-4(1H)-one, preferred substrates
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-
?
2-pentyl-4(1H)-quinolone + NADH + H+ + O2
3-hydroxy-2-pentyl-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
the alkyl side chain of 2-heptyl-4-quinolone is critical for PqsH activity with the highest activity observed for alkyl chain lengths of 7 and 9 carbons
-
-
?
2-pentylquinolin-4(1H)-one + NADH + H+ + O2
3-hydroxy-2-pentyl-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
-
-
-
?
2-propyl-4(1H)-quinolone + NADH + H+ + O2
3-hydroxy-2-propyl-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
the alkyl side chain of 2-heptyl-4-quinolone is critical for PqsH activity with the highest activity observed for alkyl chain lengths of 7 and 9 carbons
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-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-heptyl-4(1H)-quinolone + NADH + H+ + O2
2-heptyl-3-hydroxy-4(1H)-quinolone + NAD+ + H2O
show the reaction diagram
PqsH catalyzes the terminal step in biosynthesis of the Pseudomonas quinolone signal molecule 2-heptyl-3-hydroxy-4(1H)-quinolone. Under anaerobic conditions 2-heptyl-3-hydroxy-4(1H)-quinolone is not produced. The enzyme is a biochemical regulator of Pseudomonas quinolone signal controlled social behaviors in Pseudomonas aeruginosa
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
kcat/KM for NADH is 20fold higher than kcat/Km for NADPH
NADPH
kcat/KM for NADH is 20fold higher than kcat/Km for NADPH
riboflavin
flavin-dependent monooxygenase, riboflavin is included in the assay
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00011
2-heptyl-4(1H)-quinolone
pH 8.0, 25°C
0.00013
2-nonyl-4(1H)-quinolone
pH 8.0, 25°C
0.0016
2-pentyl-4(1H)-quinolone
pH 8.0, 25°C
0.014
2-propyl-4(1H)-quinolone
pH 8.0, 25°C
0.032
NADH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
0.74
NADPH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
0.00052
O2
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.7
2-heptyl-4(1H)-quinolone
pH 8.0, 25°C
2.5
2-nonyl-4(1H)-quinolone
pH 8.0, 25°C
3
2-pentyl-4(1H)-quinolone
pH 8.0, 25°C
2.3
2-propyl-4(1H)-quinolone
pH 8.0, 25°C
3.2
NADH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
3.8
NADPH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
1.2
O2
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2455
2-heptyl-4(1H)-quinolone
pH 8.0, 25°C
1900
2-nonyl-4(1H)-quinolone
pH 8.0, 25°C
190
2-pentyl-4(1H)-quinolone
pH 8.0, 25°C
17
2-propyl-4(1H)-quinolone
pH 8.0, 25°C
100
NADH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
5.1
NADPH
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
2308
O2
pH 8.0, 25°C, cosubstrate: 2-heptyl-4(1H)-quinolone
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
PqsH catalyzes the terminal step in biosynthesis of the Pseudomonas quinolone signal molecule 2-heptyl-3,4-dihydroxyquinoline. Under anaerobic conditions 2-heptyl-3-hydroxy-4(1H)-quinolone is not produced. The enzyme is a biochemical regulator of Pseudomonas Quinolone Signal controlled social behaviors in Pseudomonas aeruginosa
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
86000
x * 86000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 86000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, purified fusion protein can be stored for one week without loss of enzymatic activity
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
overexpression of recombinant enzyme in Escherichia coli both with and without a N-terminal fusion with the maltose binding protein
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
farnesol suppresses the transcription and protein expression. Farnesol inhibits the expression of PQS signal synthase coding genes (pqsABCDE and pqsH) in the PQS system, but does not inhibit the expression of the PQS signal receptor coding gene pqsR
expression is influenced by the las/rhl systems. Pseudomonas quinolone signal synthesis might be regulated by the balance between the expression of the pqsA-D/phnAB, pqsH, antABC, and catBCA gene loci
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Choi, Y.; Park, H.Y.; Park, S.J.; Park, S.J.; Kim, S.K.; Ha, C.; Im, S.J.; Lee, J.H.
Growth phase-differential quorum sensing regulation of anthranilate metabolism in Pseudomonas aeruginosa
Mol. Cells
32
57-65
2011
Pseudomonas aeruginosa
Manually annotated by BRENDA team
Schertzer, J.W., Brown, S.A.; Whiteley, M.
Oxygen levels rapidly modulate Pseudomonas aeruginosa social behaviours via substrate limitation of PqsH
Mol. Microbiol.
77
1527-1538
2010
Pseudomonas aeruginosa (Q9I0Q0)
Manually annotated by BRENDA team
Ritzmann, N.; Drees, S.; Fetznera, S.
Signal synthase-type versus catabolic monooxygenases retracing 3-hydroxylation of 2-alkylquinolones and their N-oxides by Pseudomonas aeruginosa and other pulmonary pathogens
Appl. Environ. Microbiol.
87
e02241
2021
Microbulbifer sp. HZ11, Mycobacteroides abscessus (B1MFK1), Pseudomonas aeruginosa (Q9I0Q0), Mycobacteroides abscessus DSM 44196 (B1MFK1), Pseudomonas aeruginosa DSM 22644 (Q9I0Q0)
Manually annotated by BRENDA team
Li, W.; Zeng, T.; Xie, X.; Shi, Q.; Li, C.
Inhibition of the pqsABCDE and pqsH in the pqs quorum sensing system and related virulence factors of the Pseudomonas aeruginosa PAO1 strain by farnesol
Int. Biodeter. Biodegrad.
151
104956
2020
Pseudomonas aeruginosa (Q9I0Q0)
-
Manually annotated by BRENDA team