KEGG ENZYME: 2.3.1.230

ENZYME: 2.3.1.230

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

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)

R10589 R10590 R11589 R11590

Substrate

octanoyl-CoA [CPD:C01944];
(2-aminobenzoyl)acetate [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

ec01110

Biosynthesis of secondary metabolites

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

PSG:	G655_20310 G655_20315

PRP:	M062_05435 M062_05440

PAEP:

PA1S_20980 PA1S_20985

PAER:

PA1R_gp4594 PA1R_gp4595

PAEM:

U769_20825 U769_20830

PAEL:

T223_22105 T223_22110

PAES:

SCV20265_4444 SCV20265_4445

PAEU:

BN889_01049(pqsB) BN889_01050(pqsC)

PAEG:

AI22_12955 AI22_12960

PAEC:

M802_1027 M802_1028

PAEO:

M801_1030 M801_1031

PPAA:

B7D75_20135 B7D75_20140

SECH:

B18_16615 B18_16620

» show all

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

DBGET integrated database retrieval system