KEGG   ENZYME: 2.3.1.230Help
Entry
EC 2.3.1.230                Enzyme                                 

Name
2-heptyl-4(1H)-quinolone synthase
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
malonyl-CoA:anthraniloyl-CoA C-acetyltransferase (decarboxylating)
Reaction(IUBMB)
(1) 3-oxodecanoate + anthraniloyl-CoA = CoA + 2-heptyl-4(1H)-quinolone + CO2 + H2O [RN:R10589];
(2) malonyl-CoA + anthraniloyl-CoA = 2 CoA + 4-hydroxy-2(1H)-quinolone + CO2 [RN:R10590]
Reaction(KEGG)
Substrate
3-oxodecanoate [CPD:C20714];
anthraniloyl-CoA [CPD:C02247];
malonyl-CoA [CPD:C00083]
Product
CoA [CPD:C00010];
2-heptyl-4(1H)-quinolone [CPD:C20643];
CO2 [CPD:C00011];
H2O [CPD:C00001];
4-hydroxy-2(1H)-quinolone [CPD:C16716]
Comment
The enzyme from the Gram-negative bacterium Pseudomonas aeruginosa is involved in the biosynthesis of 2-heptyl-4-hydroxyquinoline and 2,4-dihydroxyquinoline. 2-Heptyl-4-hydroxyquinoline is a signal molecule, that is involved in regulation of virulence factor production and biofilm formation. The enzyme shows a broad specificity and is involved in the synthesis of a wide array of additional 2-alkyl-4(1H)-quinolones synthesized by the organism.
History
EC 2.3.1.230 created 2013
Orthology
K18003  
2-heptyl-4(1H)-quinolone synthase
Genes
PAE: 
PA0999(pqsD)
PAEV: 
N297_1032(pqsD)
PAEI: 
N296_1032(pqsD)
PAU: 
PAP: 
PSPA7_4399(fabH1)
PAG: 
PAF: 
PNC: 
PAEB: 
PDK: 
PSG: 
PRP: 
PAEP: 
PAER: 
PAEM: 
PAEL: 
PAES: 
PAEU: 
PAEG: 
PAEC: 
M802_1029(pqsD)
PAEO: 
M801_1032(pqsD)
 » show all
Taxonomy
Reference
1  [PMID:18728009]
  Authors
Zhang YM, Frank MW, Zhu K, Mayasundari A, Rock CO
  Title
PqsD is responsible for the synthesis of 2,4-dihydroxyquinoline, an extracellular metabolite produced by Pseudomonas aeruginosa.
  Journal
J. Biol. Chem. 283 (2008) 28788-94.
  Sequence
[pae:PA0999]
Reference
2  [PMID:19694421]
  Authors
Bera AK, Atanasova V, Robinson H, Eisenstein E, Coleman JP, Pesci EC, Parsons JF
  Title
Structure of PqsD, a Pseudomonas quinolone signal biosynthetic enzyme, in complex with anthranilate.
  Journal
Biochemistry. 48 (2009) 8644-55.
Reference
3  [PMID:21425231]
  Authors
Pistorius D, Ullrich A, Lucas S, Hartmann RW, Kazmaier U, Muller R
  Title
Biosynthesis of 2-Alkyl-4(1H)-quinolones in Pseudomonas aeruginosa: potential for therapeutic interference with pathogenicity.
  Journal
Chembiochem. 12 (2011) 850-3.
Reference
4  [PMID:22992202]
  Authors
Storz MP, Maurer CK, Zimmer C, Wagner N, Brengel C, de Jong JC, Lucas S, Musken M, Haussler S, Steinbach A, Hartmann RW
  Title
Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of small-molecule inhibitors.
  Journal
J. Am. Chem. Soc. 134 (2012) 16143-6.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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