KEGG   ORTHOLOGY: K18001Help
Entry
K18001                      KO                                     

Name
pqsB
Definition
2-heptyl-4(1H)-quinolone synthase subunit PqsB [EC:2.3.1.230]
Pathway
ko00405  Phenazine biosynthesis
ko01130  Biosynthesis of antibiotics
ko02024  Quorum sensing
ko02025  Biofilm formation - Pseudomonas aeruginosa
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00405 Phenazine biosynthesis
    K18001  pqsB; 2-heptyl-4(1H)-quinolone synthase subunit PqsB
 09140 Cellular Processes
  09145 Cellular community - prokaryotes
   02024 Quorum sensing
    K18001  pqsB; 2-heptyl-4(1H)-quinolone synthase subunit PqsB
   02025 Biofilm formation - Pseudomonas aeruginosa
    K18001  pqsB; 2-heptyl-4(1H)-quinolone synthase subunit PqsB
Enzymes [BR:ko01000]
 2. Transferases
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.230  2-heptyl-4(1H)-quinolone synthase
     K18001  pqsB; 2-heptyl-4(1H)-quinolone synthase subunit PqsB
BRITE hierarchy
Other DBs
RN: R10589 R10590 R11589 R11590
COG: COG0332
Genes
PAE: PA0997(pqsB)
PAEV: N297_1030
PAEI: N296_1030
PAU: PA14_51420(pqsB)
PAP: PSPA7_4401
PAG: PLES_43281(pqsB)
PAF: PAM18_4051(pqsB)
PNC: NCGM2_1851(pqsB)
PAEB: NCGM1900_1671(pqsB)
PDK: PADK2_20755
PAEP: PA1S_20985
PAEM: U769_20830
PAEL: T223_22110
PAEU: BN889_01049(pqsB)
PAEG: AI22_12955
PAEC: M802_1027
PAEO: M801_1030
 » show all
TaxonomyKoalaUniProt
Reference
  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 48:8644-55 (2009)
DOI:10.1021/bi9009055

KEGG   ORTHOLOGY: K18002Help
Entry
K18002                      KO                                     

Name
pqsC
Definition
2-heptyl-4(1H)-quinolone synthase subunit PqsC [EC:2.3.1.230]
Pathway
ko00405  Phenazine biosynthesis
ko01130  Biosynthesis of antibiotics
ko02024  Quorum sensing
ko02025  Biofilm formation - Pseudomonas aeruginosa
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00405 Phenazine biosynthesis
    K18002  pqsC; 2-heptyl-4(1H)-quinolone synthase subunit PqsC
 09140 Cellular Processes
  09145 Cellular community - prokaryotes
   02024 Quorum sensing
    K18002  pqsC; 2-heptyl-4(1H)-quinolone synthase subunit PqsC
   02025 Biofilm formation - Pseudomonas aeruginosa
    K18002  pqsC; 2-heptyl-4(1H)-quinolone synthase subunit PqsC
Enzymes [BR:ko01000]
 2. Transferases
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.230  2-heptyl-4(1H)-quinolone synthase
     K18002  pqsC; 2-heptyl-4(1H)-quinolone synthase subunit PqsC
BRITE hierarchy
Other DBs
RN: R10589 R10590 R11589 R11590
COG: COG0332
Genes
PAE: PA0998(pqsC)
PAEV: N297_1031
PAEI: N296_1031
PAU: PA14_51410(pqsC)
PAP: PSPA7_4400
PAG: PLES_43271(pqsC)
PAF: PAM18_4050(pqsC)
PNC: NCGM2_1852(pqsC)
PAEB: NCGM1900_1670(pqsC)
PDK: PADK2_20750
PAEP: PA1S_20980
PAEM: U769_20825
PAEL: T223_22105
PAEU: BN889_01050(pqsC)
PAEG: AI22_12960
PAEC: M802_1028
PAEO: M801_1031
 » show all
TaxonomyKoalaUniProt
Reference
  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 48:8644-55 (2009)
DOI:10.1021/bi9009055

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-aminobenzoyl)acetate octanoyltransferase
Reaction(IUBMB)
octanoyl-CoA + (2-aminobenzoyl)acetate = 2-heptyl-4-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-aminobenzoyl)acetate = 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-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-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-aminobenzoyl)acetate, 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
ec00405  Phenazine biosynthesis
ec01130  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: N297_1030 N297_1031
PAEI: N296_1030 N296_1031
PAU: PA14_51410(pqsC) PA14_51420(pqsB)
PAP: PSPA7_4400 PSPA7_4401
PAG: PLES_43271(pqsC) PLES_43281(pqsB)
PAF: PAM18_4050(pqsC) PAM18_4051(pqsB)
PNC: NCGM2_1851(pqsB) NCGM2_1852(pqsC)
PAEB: NCGM1900_1670(pqsC) NCGM1900_1671(pqsB)
PDK: PADK2_20750 PADK2_20755
PAEU: BN889_01049(pqsB) BN889_01050(pqsC)
 » 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 20:1481-91 (2013)
DOI:10.1016/j.chembiol.2013.09.021
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 291:6610-24 (2016)
DOI:10.1074/jbc.M115.708453
  Sequence
[pae:PA0998]
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.230
IUBMB Enzyme Nomenclature: 2.3.1.230
ExPASy - ENZYME nomenclature database: 2.3.1.230
BRENDA, the Enzyme Database: 2.3.1.230

KEGG   REACTION: R11590Help
Entry
R11590                      Reaction                               

Name
octanoyl-CoA:2-aminobenzoylacetate octanoyltransferase
Definition
1-(2-Aminophenyl)decane-1,3-dione <=> 2-Heptyl-4(1H)-quinolone + H2O
Equation
Comment
multi-step reaction
Enzyme
Pathway
rn00405  Phenazine biosynthesis
rn01130  Biosynthesis of antibiotics
Orthology
K18001  2-heptyl-4(1H)-quinolone synthase subunit PqsB [EC:2.3.1.230]
K18002  2-heptyl-4(1H)-quinolone synthase subunit PqsC [EC:2.3.1.230]
Other DBs
RHEA: 50411

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