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Literature summary extracted from

  • Deschamps, J.D.; Ogunsola, A.F.; Jameson, J.B.; Yasgar, A.; Flitter, B.A.; Freedman, C.J.; Melvin, J.A.; Nguyen, J.V.; Maloney, D.J.; Jadhav, A.; Simeonov, A.; Bomberger, J.M.; Holman, T.R.
    Biochemical and cellular characterization and inhibitor discovery of Pseudomonas aeruginosa 15-lipoxygenase (2016), Biochemistry, 55, 3329-3340 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.33 gene loxA, recombinant expression of N-terminally His6-tagged enzyme LoxA in Escherichia coli strain BL21(DE3) Pseudomonas aeruginosa

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.33 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
-
 Pseudomonas aeruginosa
1.13.11.33 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
-
 Pseudomonas aeruginosa
1.13.11.33 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
-
 Pseudomonas aeruginosa
1.13.11.33 1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
-
 Pseudomonas aeruginosa
1.13.11.33 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
-
 Pseudomonas aeruginosa
1.13.11.33 2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
-
 Pseudomonas aeruginosa
1.13.11.33 2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
-
 Pseudomonas aeruginosa
1.13.11.33 4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
-
 Pseudomonas aeruginosa
1.13.11.33 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
-
 Pseudomonas aeruginosa
1.13.11.33 4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
-
 Pseudomonas aeruginosa
1.13.11.33 6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
-
 Pseudomonas aeruginosa
1.13.11.33 7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
-
 Pseudomonas aeruginosa
1.13.11.33 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
-
 Pseudomonas aeruginosa
1.13.11.33 methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
-
 Pseudomonas aeruginosa
1.13.11.33 additional information inhibitor library screening, none selectively targets LoxA over the human LOX isozymes, overview Pseudomonas aeruginosa
1.13.11.33 N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
-
 Pseudomonas aeruginosa

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.13.11.33 additional information
-
 additional information Michaelis-Menten steady-state kinetics Pseudomonas aeruginosa
1.13.11.33 0.007
-
 linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 0.012
-
 arachidonate pH 6.5-7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 0.013
-
 arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.13.11.33 extracellular the enzyme is secreted Pseudomonas aeruginosa
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.33 arachidonate + O2 Pseudomonas aeruginosa
-
 (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.33 Pseudomonas aeruginosa Q9I4G8
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.13.11.33 recombinant N-terminally His6-tagged enzyme LoxA from Escherichia coli strain BL21(DE3) by nickel affinity chromatography Pseudomonas aeruginosa

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.33 alpha-linoleic acid + O2 72% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 arachidonate + O2
-
 Pseudomonas aeruginosa (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
 ?
1.13.11.33 arachidonate + O2 best substrate Pseudomonas aeruginosa (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
-
 ?
1.13.11.33 dihomo-gamma-linolenic acid + O2 44% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 docosahexaenoic acid + O2 72% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 eicosadienoic acid + O2 33% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 eicosapentanoic acid + O2 61% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 gamma-linolenic acid + O2 44% activity compared to arachidonate Pseudomonas aeruginosa ?
-
 ?
1.13.11.33 linoleic acid + O2 78% activity compared to arachidonate Pseudomonas aeruginosa (9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
-
 ?
1.13.11.33 additional information enzyme LoxA is capable of efficiently catalyzing the peroxidation of a broad range of free fatty acid substrates, e.g. arachidonate and linoleate with high positional specificity, indicating a 15-LOX, its mechanism includes hydrogen atom abstraction. LoxA also does not react with 5- or 15-15-hydroperoxyicosatetraenoates, or phosphoester fatty acids Pseudomonas aeruginosa ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.33 15-lipoxygenase
-
 Pseudomonas aeruginosa
1.13.11.33 LoxA
-
 Pseudomonas aeruginosa

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.13.11.33 22
-
 assay at Pseudomonas aeruginosa

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.13.11.33 2 8 linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 86
-
 arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 157
-
 arachidonate pH 7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 181
-
 arachidonate pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.13.11.33 6.5
-
 assay at Pseudomonas aeruginosa

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.33 0.0041
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
1.13.11.33 0.0045
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
1.13.11.33 0.0058
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
1.13.11.33 0.0067
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
1.13.11.33 0.008
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
1.13.11.33 0.0101
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
1.13.11.33 0.011
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
1.13.11.33 0.0114
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
1.13.11.33 0.0131
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
1.13.11.33 0.0138
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
1.13.11.33 0.0162
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
1.13.11.33 0.02
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
1.13.11.33 0.046
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
1.13.11.33 0.078
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa 2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
1.13.11.33 0.1
-
 pH 6.5, 2°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide

Expression

EC Number Organism Comment Expression
1.13.11.33 Pseudomonas aeruginosa the level of LoxA expression is increased when Pseudomonas aeruginosa undergoes the transition to a biofilm mode of growth up

General Information

EC Number General Information Comment Organism
1.13.11.33 physiological function enzyme LoxA is a poor catalyst against phosphoester fatty acids, suggesting that LoxA is not involved in membrane decomposition. LoxA also does not react with 5- or 15-HETEs, indicating poor involvement in lipoxin production. The level of LoxA expression is increased when Pseudomonas aeruginosa undergoes the transition to a biofilm mode of growth, but LoxA is not required for biofilm growth on abiotic surfaces. LoxA does appear to be required for biofilm growth in association with the host airway epithelium, suggesting a role for LoxA in mediating bacterium-host interactions during colonization Pseudomonas aeruginosa

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.13.11.33 0.0038
-
 linoleic acid pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 0.0066
-
 arachidonate pH 7.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 0.013
-
 arachidonate pH 7.0, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa
1.13.11.33 0.016
-
 arachidonate pH 6.5, 22°C, recombinant His6-tagged enzyme Pseudomonas aeruginosa