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anthraniloyl-CoA + L-cysteinyl-[PqsD protein]
S-anthraniloyl-L-cysteinyl-[PqsD protein] + CoA
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2,4-dihydroxyquinoline + 2 CoA + CO2 + ?
-
in vitro overall reaction
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
S-anthraniloyl-L-cysteinyl-[PqsD protein] + malonyl-CoA
2-aminobenzoylacetyl-CoA + CO2 + L-cysteinyl-[PqsD protein]
-
-
-
?
additional information
?
-
initial catalytic step of PqsD is the transfer of the anthraniloyl moiety to residue Cys112 under hydrolysis of the anthraniloyl-CoA thioester. The second step in the reaction that leads to Cys112-anthraniloyl and CoA is a concerted reaction mechanism. The deprotonated sulfur atom of Cys112 performs a nucleophilic attack at the carbonyl carbon of anthraniloyl-CoA while the proton at Nepsilon of His257 is simultaneously shifted to the sulfur atom of CoA. During the reaction, His257 switches its protonation pattern. Only Nepsilon is protonated in the reactant state, whereas the uptake of a proton at Ndelta to deprotonation of Cys112 leads to a doubly protonated (positively charged) intermediate. From there, the proton at Nepsilon is subsequently transferred to the sulfur of CoA, leading to a net neutral product
-
-
?
anthraniloyl-CoA + malonyl-CoA

2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
overall reaction
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
anthraniloyl-CoA + malonyl-CoA
2-aminobenzoylacetyl-CoA + CoA + CO2
-
-
-
?
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(2-nitrophenyl)(phenyl)methanol
(2E)-3-(thiophen-3-yl)prop-2-enoic acid
-
(2R)-2,4-dihydroxy-N-(3-[[4-hydroxy-4-(2-nitrophenyl)butyl]amino]-3-oxopropyl)-3,3-dimethylbutanamide
-
(E)-1-(2-chloro-8-methylquinolin-3-yl)-N-[3-fluoro-4-(morpholin-4-yl)phenyl]methanimine
-
(E)-1-(2-chloroquinolin-3-yl)-N-[3-fluoro-4-(morpholin-4-yl)phenyl]methanimine
-
1-(1-aminonaphthalen-2-yl)-2-chloroethan-1-one
strong inhibition
1-(2-aminophenyl)-2-chloroethan-1-one
strong inhibition
1-(2-nitrophenyl)propan-1-ol
-
1-(7-amino-2,3-dihydro-1,4-benzodioxin-6-yl)-2-chloroethan-1-one
strong inhibition
1-methyl-2-methylideneimidazolidine
-
2-(3,4-dichlorobenzene-1-sulfonyl)-4-(1H-tetrazol-1-yl)pyrimidine
-
2-(benzenesulfonyl)-4-(1H-tetrazol-1-yl)pyrimidine
-
2-(hexane-1-sulfonyl)-4-(1H-1,2,3-triazol-1-yl)pyrimidine
-
2-(methanesulfonyl)-4-(1H-1,2,3-triazol-1-yl)pyrimidine
-
2-(methanesulfonyl)-4-(1H-tetrazol-1-yl)pyrimidine
-
2-(methanesulfonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrimidine
-
2-(methanesulfonyl)-4-phenoxy-6-(1H-1,2,3-triazol-1-yl)pyrimidine
-
2-bromo-1-(pyridin-2-yl)ethan-1-one
slight inhibition
2-chloro-1-(1H-indol-7-yl)ethan-1-one
strong inhibition
2-chloro-1-(2,4-difluorophenyl)ethan-1-one
strong inhibition
2-chloro-1-phenylethan-1-one
strong inhibition
2-chloro-N-(3-chloro-2-methylphenyl)acetamide
strong inhibition
2-chloro-N-(4-methylphenyl)acetamide
-
2-[(biphenyl-4-ylcarbonyl)amino]-3-chlorobenzoic acid
-
strong inhibition, without inhibiting RNA polymerase
2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-chlorobenzoic acid
-
2-[([1,1'-biphenyl]-4-carbonyl)amino]benzoic acid
-
2-[3-(diethylsulfamoyl)benzamido]-6-hydroxybenzoic acid
-
2-[3-hydroxy-3-(2-nitrophenyl)propyl]-1H-isoindole-1,3(2H)-dione
-
3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide
-
3-(3,4-dihydroxyphenyl)propanoic acid
-
3-(3-carboxypropanamido)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
-
3-([[(1S)-1-carboxy-2-phenylethyl]carbamoyl]amino)-7-methoxy-4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylic acid
-
3-([[(1S)-1-carboxy-3-phenylpropyl]carbamoyl]amino)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
-
3-([[(S)-carboxy(phenyl)methyl]carbamoyl]amino)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
-
3-chlorobicyclo[2.2.1]heptan-2-one
slight inhibition
3-[[benzyl(ethyl)carbamoyl]amino]-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
-
4-[3-(diethylsulfamoyl)benzamido][1,1'-biphenyl]-3-carboxylic acid
-
benzyl 3-(3,4-dihydroxyphenyl)propanoate
-
methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
methyl 4-(3,4-dihydroxyphenyl)butanoate
-
N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide
-
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide
-
N-([2-carboxy-5-[4'-(hydroxymethyl)[1,1'-biphenyl]-4-yl]thiophen-3-yl]carbamoyl)-L-phenylalanine
-
N-([2-carboxy-5-[4-(2-chloroacetamido)phenyl]thiophen-3-yl]carbamoyl)-L-phenylalanine
-
N-[(2-carboxy-5-phenylthiophen-3-yl)carbamoyl]-L-phenylalanine
-
N-[(2-carboxy-5-[4'-[hydroxy(2-nitrophenyl)methyl][1,1'-biphenyl]-4-yl]thiophen-3-yl)carbamoyl]-L-phenylalanine
-
N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide
-
-
N-[[2-carboxy-5-(4-hydroxyphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
-
N-[[2-carboxy-5-(4-methoxy-2-methylphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
-
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-4-chloro-L-phenylalanine
-
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
-
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-L-tyrosine
-
N-[[3-(furan-2-yl)-1H-pyrazol-5-yl]methyl]-2-(4-methylpiperazin-1-yl)pyrimidin-4-amine
-
propan-2-yl 3-(3,4-dihydroxyphenyl)propanoate
-
tert-butyl chloroacetate
-
[4-(2-chloropropanoyl)phenyl]acetic acid
slight inhibition
additional information
inhibitor development targeting enzyme PqsD, development of a competitive in situ labeling strategy using an electrophilic activity-based probe and target protein expressing Escherichia coli cells
-
(2-nitrophenyl)(phenyl)methanol

-
at a concentration of 250 microM, both the 2-heptyl-4-hydroxyquinoline and Pseudomonas quinolone signal levels are strongly reduced by 77 and 42%, respectively, in Pseudomonas aeruginosa PA14 cultures. The 2,4-dihydroxyquinoline level increases in the presence of the compound. Addition of the compound to a 24 h old biofilm reduces the biovolume of the biofilm by 38% within a 24 h incubation period
(2-nitrophenyl)(phenyl)methanol
-
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0.0032
(2-nitrophenyl)(phenyl)methanol
0.0079
(2R)-2,4-dihydroxy-N-(3-[[4-hydroxy-4-(2-nitrophenyl)butyl]amino]-3-oxopropyl)-3,3-dimethylbutanamide
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0156
(E)-1-(2-chloro-8-methylquinolin-3-yl)-N-[3-fluoro-4-(morpholin-4-yl)phenyl]methanimine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0129
(E)-1-(2-chloroquinolin-3-yl)-N-[3-fluoro-4-(morpholin-4-yl)phenyl]methanimine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0012
1-(1-aminonaphthalen-2-yl)-2-chloroethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0019
1-(2-aminophenyl)-2-chloroethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0011
1-(2-nitrophenyl)propan-1-ol
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0022
1-(7-amino-2,3-dihydro-1,4-benzodioxin-6-yl)-2-chloroethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0004
2-(3,4-dichlorobenzene-1-sulfonyl)-4-(1H-tetrazol-1-yl)pyrimidine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0017
2-(benzenesulfonyl)-4-(1H-tetrazol-1-yl)pyrimidine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0017
2-(hexane-1-sulfonyl)-4-(1H-1,2,3-triazol-1-yl)pyrimidine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0032
2-(methanesulfonyl)-4-phenoxy-6-(1H-1,2,3-triazol-1-yl)pyrimidine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0025
2-chloro-1-(1H-indol-7-yl)ethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0013
2-chloro-1-(2,4-difluorophenyl)ethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0018
2-chloro-1-phenylethan-1-one
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0021
2-chloro-N-(3-chloro-2-methylphenyl)acetamide
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.155
2-chloro-N-(4-methylphenyl)acetamide
Pseudomonas aeruginosa
pH not specified in the publication, 37°C
0.0062
2-[(biphenyl-4-ylcarbonyl)amino]-3-chlorobenzoic acid
Pseudomonas aeruginosa
-
pH not specified in the publication, temperature not specified in the publication
0.0062
2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-chlorobenzoic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0013
2-[([1,1'-biphenyl]-4-carbonyl)amino]benzoic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0012
2-[3-(diethylsulfamoyl)benzamido]-6-hydroxybenzoic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0003
2-[3-hydroxy-3-(2-nitrophenyl)propyl]-1H-isoindole-1,3(2H)-dione
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.027
3-(3,4-dihydroxyphenyl)propanoic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.007
3-(3-carboxypropanamido)-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0237
3-([[(1S)-1-carboxy-2-phenylethyl]carbamoyl]amino)-7-methoxy-4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.006
3-[[benzyl(ethyl)carbamoyl]amino]-5-(4-methoxyphenyl)thiophene-2-carboxylic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0003
4-[3-(diethylsulfamoyl)benzamido][1,1'-biphenyl]-3-carboxylic acid
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0059
benzyl 3-(3,4-dihydroxyphenyl)propanoate
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.051
methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0079
methyl 4-(3,4-dihydroxyphenyl)butanoate
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0159
N-([(5R)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.00036
N-([2-carboxy-5-[4'-(hydroxymethyl)[1,1'-biphenyl]-4-yl]thiophen-3-yl]carbamoyl)-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.002
N-([2-carboxy-5-[4-(2-chloroacetamido)phenyl]thiophen-3-yl]carbamoyl)-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0038
N-[(2-carboxy-5-phenylthiophen-3-yl)carbamoyl]-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0014
N-[(2-carboxy-5-[4'-[hydroxy(2-nitrophenyl)methyl][1,1'-biphenyl]-4-yl]thiophen-3-yl)carbamoyl]-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0043
N-[4-hydroxy-4-(2-nitrophenyl)butyl]acetamide
Pseudomonas aeruginosa
-
pH not specified in the publication, temperature not specified in the publication
0.0216
N-[[2-carboxy-5-(4-hydroxyphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0075
N-[[2-carboxy-5-(4-methoxy-2-methylphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0138
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-4-chloro-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0005
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-L-phenylalanine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.029
N-[[2-carboxy-5-(4-methoxyphenyl)thiophen-3-yl]carbamoyl]-L-tyrosine
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0086
propan-2-yl 3-(3,4-dihydroxyphenyl)propanoate
Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0032
(2-nitrophenyl)(phenyl)methanol

Pseudomonas aeruginosa
pH and temperature not specified in the publication
0.0032
(2-nitrophenyl)(phenyl)methanol
Pseudomonas aeruginosa
-
pH not specified in the publication, temperature not specified in the publication
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Bera, A.K.; Atanasova, V.; Robinson, H.; Eisenstein, E.; Coleman, J.P.; Pesci, E.C.; Parsons, J.F.
Structure of PqsD, a Pseudomonas quinolone signal biosynthetic enzyme, in complex with anthranilate
Biochemistry
48
8644-8655
2009
Pseudomonas aeruginosa (P20582)
brenda
Storz, M.P.; Maurer, C.K.; Zimmer, C.; Wagner, N.; Brengel, C.; de Jong, J.C.; Lucas, S.; Msken, M.; Hussler, S.; Steinbach, A.; Hartmann, R.W.
Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of small-molecule inhibitors
J. Am. Chem. Soc.
134
16143-16146
2012
Pseudomonas aeruginosa
brenda
Dulcey, C.E.; Dekimpe, V.; Fauvelle, D.A.; Milot, S.; Groleau, M.C.; Doucet, N.; Rahme, L.G.; Lepine, F.; Deziel, E.
The end of an old hypothesis: the Pseudomonas signaling molecules 4-hydroxy-2-alkylquinolines derive from fatty acids, not 3-ketofatty acids
Chem. Biol.
20
1481-1491
2013
Pseudomonas aeruginosa (P20582)
brenda
Hinsberger, S.; de Jong, J.C.; Groh, M.; Haupenthal, J.; Hartmann, R.W.
Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections
Eur. J. Med. Chem.
76
343-351
2014
Pseudomonas aeruginosa
brenda
Hutter, M.C.; Brengel, C.; Negri, M.; Henn, C.; Zimmer, C.; Hartmann, R.W.; Empting, M.; Steinbach, A.
Mechanistic details for anthraniloyl transfer in PqsD: the initial step in HHQ biosynthesis
J. Mol. Model.
20
2255
2014
Pseudomonas aeruginosa (P20582)
brenda
Drees, S.L.; Fetzner, S.
PqsE of Pseudomonas aeruginosa acts as pathway-specific thioesterase in the biosynthesis of alkylquinolone signaling molecules
Chem. Biol.
22
611-618
2015
Pseudomonas aeruginosa (P20582)
brenda
Zhou, Z.; Ma, S.
Recent advances in the discovery of PqsD inhibitors as antimicrobial agents
ChemMedChem
12
420-425
2017
Pseudomonas aeruginosa (P20582)
brenda
Prothiwa, M.; Englmaier, F.; Boettcher, T.
Competitive live-cell profiling strategy for discovering inhibitors of the quinolone biosynthesis of Pseudomonas aeruginosa
J. Am. Chem. Soc.
140
14019-14023
2018
Pseudomonas aeruginosa (P20582), Pseudomonas aeruginosa ATCC 15692 (P20582), Pseudomonas aeruginosa 1C (P20582), Pseudomonas aeruginosa PRS 101 (P20582), Pseudomonas aeruginosa DSM 22644 (P20582), Pseudomonas aeruginosa CIP 104116 (P20582), Pseudomonas aeruginosa LMG 12228 (P20582), Pseudomonas aeruginosa JCM 14847 (P20582)
brenda