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Literature summary for 1.13.11.58 extracted from

  • Boeglin, W.E.; Itoh, A.; Zheng, Y.; Coffa, G.; Howe, G.A.; Brash, A.R.
    Investigation of substrate binding and product stereochemistry issues in two linoleate 9-lipoxygenases (2008), Lipids, 43, 979-987.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
heterologously expressed in Escherichia coli Arabidopsis thaliana
heterologously expressed in Escherichia coli Solanum lycopersicum

Protein Variants

Protein Variants Comment Organism
A562G the product of the wild-type enzyme is 98.8% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 1.2% (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate. The product of mutant enzyme A562G is 68.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 31.1% (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate. Wild-type enzyme converts anandamide mainly to (11S)-hydroperoxyanandamide (99.4%). The mutant A562G forms (11S)-hydroperoxyanandamide and 15R-hydroperoxyanandamide in the ratio 3:2 Arabidopsis thaliana
A564G the product of the wild-type enzyme is 99.1% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 0.9% (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate. The product of mutant enzyme A562G is 68.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 31.1% (9Z,11E,13S)-13-hydroperoxy-11,13-octadecadienoate. Wild-type enzyme converts anandamide mainly to (11S)-hydroperoxyanandamide (71%), plus 16% (5S)-hydroperoxyanandamide. The mutant enzyme A564G forms two additional prominent products, 15-hydroperoxyanandamide (34%) and 9-hydroperoxyanandamide (19%) Solanum lycopersicum

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana Q06327
-
-
Solanum lycopersicum P38415
-
-

Purification (Commentary)

Purification (Comment) Organism
partially purified by nickel affinity chromatography using a N-terminal (His)6-tag Arabidopsis thaliana
partially purified by nickel affinity chromatography using a N-terminal (His)6-tag Solanum lycopersicum

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
linoleate + O2
-
Arabidopsis thaliana (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate the product of the wild-type enzyme is 98.8% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 1.2% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate. The product of mutant enzyme A562G is 68.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 31.1% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate ?
linoleate + O2
-
Solanum lycopersicum (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate the product of the wild-type enzyme is 99.1% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 0.9% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate. The product of mutant enzyme A564G is 59.9% (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and 40.1% (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate ?
additional information from arachidonate the wild-type enzyme forms 11-hydroxyeicosatetraenoic acid and 5-hydroxyeicosatetraenoic acid in essentially equal amounts (38-39%), 11% 8-hydroxyeicosatetraenoic acid, 4% 12-hydroxyeicosatetraenoic acid, 3% 15-hydroxyeicosatetraenoic acid and 2% 9-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to (11S)-hydroperoxyanandamide (71%), plus 16% (5S)-hydroperoxyanandamide. The mutant enzyme A564G forms two additional prominent products, 15-hydroperoxyanandamide (34%) and 9-hydroperoxyanandamide (19%). No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry Solanum lycopersicum ?
-
?
additional information from arachidonate the wild-type enzyme forms 47% 11-hydroxyeicosatetraenoic acid, 23% 5-hydroxyeicosatetraenoic acid, 11% 9-hydroxyeicosatetraenoic acid, 9% 12-hydroxyeicosatetraenoic acid, 4.5% 8-hydroxyeicosatetraenoic acid and 4.5% 15-hydroxyeicosatetraenoic acid. Wild-type enzyme converts anandamide mainly to 11S-hydroperoxyanandamide (99.4%). The mutant A562G forms (11S)-hydroperoxyanandamide and (15R)-hydroperoxyanandamide in the ratio 3:2. No activity detected with 1-palmitoyl-2-linoleoylphosphatidylcholine. A model is tested that predicts a relationship between substrate binding orientation and product stereochemistry Arabidopsis thaliana ?
-
?

Synonyms

Synonyms Comment Organism
9-LOX
-
Arabidopsis thaliana
9-LOX
-
Solanum lycopersicum
AtLOX1
-
Arabidopsis thaliana
linoleate 9S-lipoxygenase
-
Solanum lycopersicum
LoxA
-
Solanum lycopersicum

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
310
-
linoleate
-
Arabidopsis thaliana
390
-
linoleate
-
Solanum lycopersicum

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
-
Arabidopsis thaliana
6
-
-
Solanum lycopersicum

pH Range

pH Minimum pH Maximum Comment Organism
8 9 pH 8: 30% of optimal activity, pH 9: about 15% of maximal activity Solanum lycopersicum