KEGG   ENZYME: 2.3.1.230Help
Entry
EC 2.3.1.230                Enzyme                                 

Name
2-heptyl-4(1H)-quinolone synthase;
pqsBC (gene names);
malonyl-CoA:anthraniloyl-CoA C-acetyltransferase (decarboxylating)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
octanoyl-CoA:2-aminobenzoylacetate octanoyltransferase
Reaction(IUBMB)
octanoyl-CoA + 2-aminobenzoylacetate = 2-heptyl-4(1H)-quinolone + CoA + CO2 + H2O (overall reaction) [RN:R10589];
(1a) octanoyl-CoA + L-cysteinyl-[PqsC protein] = S-octanoyl-L-cysteinyl-[PqsC protein] + CoA [RN:R10590];
(1b) S-octanoyl-L-cysteinyl-[PqsC protein] + 2-aminobenzoylacetate = 1-(2-aminophenyl)decane-1,3-dione + CO2 + L-cysteinyl-[PqsC protein] [RN:R11589];
(1c) 1-(2-aminophenyl)decane-1,3-dione = 2-heptyl-4(1H)-quinolone + H2O [RN:R11590]
Reaction(KEGG)
Substrate
octanoyl-CoA [CPD:C01944];
2-aminobenzoylacetate [CPD:C21453];
L-cysteinyl-[PqsC protein];
S-octanoyl-L-cysteinyl-[PqsC protein];
1-(2-aminophenyl)decane-1,3-dione [CPD:C21490]
Product
2-heptyl-4(1H)-quinolone [CPD:C20643];
CoA [CPD:C00010];
CO2 [CPD:C00011];
H2O [CPD:C00001];
S-octanoyl-L-cysteinyl-[PqsC protein];
1-(2-aminophenyl)decane-1,3-dione [CPD:C21490];
L-cysteinyl-[PqsC protein]
Comment
The enzyme, characterized from the bacterium Pseudomonas aeruginosa, is a heterodimeric complex. The PqsC subunit acquires an octanoyl group from octanoyl-CoA and attaches it to an internal cysteine residue. Together with the PqsB subunit, the proteins catalyse the coupling of the octanoyl group with 2-aminobenzoylacetate, leading to decarboxylation and dehydration events that result in closure of the quinoline ring.
History
EC 2.3.1.230 created 2013, modified 2017
Pathway
Phenazine biosynthesis
Biosynthesis of antibiotics
Orthology
K18001  
2-heptyl-4(1H)-quinolone synthase subunit PqsB
K18002  
2-heptyl-4(1H)-quinolone synthase subunit PqsC
Genes
PAE: 
PA0997(pqsB) PA0998(pqsC)
PAEV: 
PAEI: 
PAU: 
PAP: 
PAG: 
PAF: 
PNC: 
PAEB: 
PDK: 
PSG: 
PRP: 
PAEP: 
PAER: 
PAEM: 
PAEL: 
PAES: 
PAEU: 
PAEG: 
PAEC: 
PAEO: 
 » show all
Taxonomy
Reference
1  [PMID:24239007]
  Authors
Dulcey CE, Dekimpe V, Fauvelle DA, Milot S, Groleau MC, Doucet N, Rahme LG, Lepine F, Deziel E
  Title
The end of an old hypothesis: the pseudomonas signaling molecules 4-hydroxy-2-alkylquinolines derive from fatty acids, not 3-ketofatty acids.
  Journal
Chem. Biol. 20 (2013) 1481-91.
Reference
2  [PMID:26811339]
  Authors
Drees SL, Li C, Prasetya F, Saleem M, Dreveny I, Williams P, Hennecke U, Emsley J, Fetzner S
  Title
PqsBC, a Condensing Enzyme in the Biosynthesis of the Pseudomonas aeruginosa Quinolone Signal: CRYSTAL STRUCTURE, INHIBITION, AND REACTION MECHANISM.
  Journal
J. Biol. Chem. 291 (2016) 6610-24.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

DBGET integrated database retrieval system