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Information on EC 1.13.11.33 - arachidonate 15-lipoxygenase and Organism(s) Pseudomonas aeruginosa and UniProt Accession Q9I4G8

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IUBMB Comments
The product is rapidly reduced to the corresponding 15S-hydroxy compound.
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This record set is specific for:
Pseudomonas aeruginosa
UNIPROT: Q9I4G8
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The taxonomic range for the selected organisms is: Pseudomonas aeruginosa
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
15-lox, 15-lo-1, 15-lox-2, 15-lox2, arachidonate 15-lipoxygenase, soybean 15-lipoxygenase, 15-lipoxygenase-2, 15lo1, 15-hlo, 15-lipoxygenase 1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
15-lipoxygenase
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-
-
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15-LOX
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-
-
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arachidonate 15-lipoxygenase
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arachidonic acid 15-lipoxygenase
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-
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linoleic acid omega-6-lipoxygenase
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omega-6 lipoxygenase
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-
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oxygenase, arachidonate 15-lip-
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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-
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oxidation
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reduction
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dioxygenation
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PATHWAY SOURCE
PATHWAYS
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-, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
arachidonate:oxygen 15-oxidoreductase
The product is rapidly reduced to the corresponding 15S-hydroxy compound.
CAS REGISTRY NUMBER
COMMENTARY hide
82249-77-2
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
alpha-linoleic acid + O2
?
show the reaction diagram
72% activity compared to arachidonate
-
-
?
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
dihomo-gamma-linolenic acid + O2
?
show the reaction diagram
44% activity compared to arachidonate
-
-
?
docosahexaenoic acid + O2
?
show the reaction diagram
72% activity compared to arachidonate
-
-
?
eicosadienoic acid + O2
?
show the reaction diagram
33% activity compared to arachidonate
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-
?
eicosapentanoic acid + O2
?
show the reaction diagram
61% activity compared to arachidonate
-
-
?
gamma-linolenic acid + O2
?
show the reaction diagram
44% activity compared to arachidonate
-
-
?
linoleic acid + O2
(9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
show the reaction diagram
78% activity compared to arachidonate
-
-
?
arachidonic acid + O2
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid
show the reaction diagram
-
-
-
-
?
additional information
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
arachidonate + O2
(5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate
show the reaction diagram
-
-
-
?
additional information
?
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production of antiinflammatory lipid mediators by the enzyme may be a general strategy by which pathogens regulate the host-pathogen relationship
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
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1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
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1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
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1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
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1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
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2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
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2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
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4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
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4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
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4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
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6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
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7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
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8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
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methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
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N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
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additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.012 - 0.013
arachidonate
0.007
linoleic acid
pH 6.5, 22°C, recombinant His6-tagged enzyme
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
86 - 181
arachidonate
2 - 8
linoleic acid
pH 6.5, 22°C, recombinant His6-tagged enzyme
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0066 - 0.016
arachidonate
0.0038
linoleic acid
pH 6.5, 22°C, recombinant His6-tagged enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0101
1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0058
1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.008
1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.046
1-[4-[4-([[5-(3-chlorophenyl)furan-2-yl]methyl]amino)phenyl]piperazin-1-yl]ethan-1-one
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0045
1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.078
2-(4-chlorophenyl)-5-cyclohexyl-1,3,4-oxadiazole
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0067
2-[4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy]-N,N-dimethylethan-1-amine
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.011
4,4'-(2,3-dimethylbutane-1,4-diyl)di(benzene-1,2-diol)
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0131
4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.02
4-[[5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl]sulfanyl]but-2-yn-1-yl benzoate
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0114
6-[4-([1,1'-biphenyl]-2-yl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0162
7-cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0041
8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.0138
methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
0.1
N-[(5-bromo-8-hydroxy-5,6,7,8-tetrahydroquinolin-7-yl)(thiophen-2-yl)methyl]acetamide
Pseudomonas aeruginosa
pH 6.5, 2°C, recombinant His6-tagged enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
the enzyme is secreted
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Manually annotated by BRENDA team
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a significant fraction of the active protein is secreted extracellularly by an Xcp-dependent process
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Manually annotated by BRENDA team
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predominantly localized in
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant N-terminally His6-tagged enzyme LoxA from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene loxA, recombinant expression of N-terminally His6-tagged enzyme LoxA in Escherichia coli strain BL21(DE3)
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the level of LoxA expression is increased when Pseudomonas aeruginosa undergoes the transition to a biofilm mode of growth
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Vance, R.E.; Hong, S.; Gronert, K.; Serhan, C.N.; Mekalanos, J.J.
The opportunistic pathogen Pseudomonas aeruginosa carries a secretable arachidonate 15-lipoxygenase
Proc. Natl. Acad. Sci. USA
101
2135-2139
2004
Pseudomonas aeruginosa
Manually annotated by BRENDA team
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
Biochemistry
55
3329-3340
2016
Pseudomonas aeruginosa (Q9I4G8), Pseudomonas aeruginosa
Manually annotated by BRENDA team