superpathway of quinolone and alkylquinolone biosynthesis

Hermes FA, Cronan JE. The role of the Saccharomyces cerevisiae lipoate protein ligase homologue, Lip3, in lipoic acid synthesis. Yeast. 2013 Oct;30(10):415–27. PMID: 23960015; PMCID: PMC3806487.; Heeb S, Fletcher MP, Chhabra SR, Diggle SP, Williams P, Cámara M. Quinolones: from antibiotics to autoinducers. FEMS Microbiol Rev. 2011 Mar;35(2):247–74. doi: 10.1111/j.1574-6976.2010.00247.x.; Schertzer JW, Brown SA, Whiteley M. Oxygen levels rapidly modulate Pseudomonas aeruginosa social behaviours via substrate limitation of PqsH. Molecular Microbiology. 2010 Sep;77(6):1527–38. doi: 10.1111/j.1365-2958.2010.07303.x.; Bera AK, Atanasova V, Robinson H, Eisenstein E, Coleman JP, Pesci EC, Parsons JF. Structure of PqsD, a Pseudomonas Quinolone Signal Biosynthetic Enzyme, in Complex with Anthranilate. Biochemistry. 2009 Aug 20;48(36):8644–55. doi: 10.1021/bi9009055.; Zhang Y, Frank MW, Zhu K, Mayasundari A, Rock CO. PqsD Is Responsible for the Synthesis of 2,4-Dihydroxyquinoline, an Extracellular Metabolite Produced by Pseudomonas aeruginosa. Journal of Biological Chemistry. 2008 Oct;283(43):28788–94. doi: 10.1074/jbc.m804555200.; Dubern JF, Diggle SP. Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species. Mol Biosyst. 2008 Sep;4(9):882–8. doi: 10.1039/b803796p. PMID: 18704225.; Lépine F, Dekimpe V, Lesic B, Milot S, Lesimple A, Mamer OA, Rahme LG, Déziel E. PqsA is required for the biosynthesis of 2,4-dihydroxyquinoline (DHQ), a newly identified metabolite produced by Pseudomonas aeruginosa and Burkholderia thailandensis. 2007 Aug 01;388(8):839–45. doi: 10.1515/bc.2007.100.; Farrow JM, Pesci EC. Two distinct pathways supply anthranilate as a precursor of the Pseudomonas quinolone signal. J Bacteriol. 2007 May;189(9):3425–33. PMID: 17337571; PMCID: PMC1855905.; Bredenbruch F, Nimtz M, Wray V, Morr M, Mu¨ller R, Ha¨ussler S. Biosynthetic Pathway of Pseudomonas aeruginosa 4-Hydroxy-2-Alkylquinolines. J Bacteriol. 2005 Jun;187(11):3630–5. doi: 10.1128/jb.187.11.3630-3635.2005.; Déziel E, Lépine F, Milot S, He J, Mindrinos MN, Tompkins RG, Rahme LG. Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication. Proc. Natl. Acad. Sci. U.S.A. 2004 Jan 22;101(5):1339–44. doi: 10.1073/pnas.0307694100.

Metabolites

2-Heptyl-3-hydroxy-quinolone

Formula: C16H21NO2 (259.1572206)

CAS ID: 521313-35-9

2-Heptyl-4(1H)-quinolone

Formula: C16H21NO (243.1623056)

CAS ID: 2503-80-2

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Diphosphate

Formula: H4P2O7 (177.9432294)

CAS ID: 2466-09-3

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

pyruvate

Formula: C3H3O3 (87.00821880000001)

CAS ID: 57-60-3

anthranilate

Formula: C7H6NO2 (136.0398516)

CAS ID: 9031-59-8

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9



Enzyme

EC Number name full name note
1.14.13.182 2-heptyl-3-hydroxy-4(1H)-quinolone synthase 2-heptyl-4(1H)-quinolone,NADH:oxygen oxidoreductase (3-hydroxylating)
3.1.2.32 2-aminobenzoylacetyl-CoA thioesterase 2-aminobenzoylacetyl-CoA hydrolase
4.1.3.27 anthranilate synthase chorismate pyruvate-lyase (amino-accepting; anthranilate-forming)
6.2.1.32 anthranilate-CoA ligase anthranilate:CoA ligase (AMP-forming)


Proteins

Protein ID name full name
P09785 phnA anthranilate synthase component I
P09786 phnB anthranilate synthase component II
P20576 trpG anthranilate synthase component II
P20580 trpE anthranilate synthetase component I
P20581 pqsE Quinolone signal response protein
Q9I0Q0 pqsH probable FAD-dependent monooxygenase
Q9I4X3 pqsA probable coenzyme A ligase