1.13.11.58: linoleate 9S-lipoxygenase
This is an abbreviated version!
For detailed information about linoleate 9S-lipoxygenase, go to the full flat file.
Word Map on EC 1.13.11.58
-
1.13.11.58
-
linoleic
-
oxylipins
-
9-loxs
-
lipoxygenases
-
9s-hydroperoxide
-
13-lipoxygenase
-
divinyl
-
colneleic
-
trihydroxy
-
alpha-ketols
-
epoxyalcohols
-
12r-lox
-
9s-hydroperoxy-10e,12z-octadecadienoic
-
synthesis
- 1.13.11.58
-
linoleic
- oxylipins
-
9-loxs
- lipoxygenases
-
9s-hydroperoxide
-
13-lipoxygenase
-
divinyl
-
colneleic
-
trihydroxy
-
alpha-ketols
- epoxyalcohols
- 12r-lox
-
9s-hydroperoxy-10e,12z-octadecadienoic
- synthesis
Reaction
Synonyms
15-LOX, 9-lipoxygenase, 9-LO, 9-LOX, 9LOX, 9S-lipoxygenase, arachidonate 9S-LOX, AtLOX-1, AtLOX-5, AtLOX1, AtLOX5, CaLOX1, eLOX3, epidermal lipoxygenase-3, GhLOX1, L-2, linoleate 9-lipoxygenase, linoleate 9S-lipoxygenase, linoleate 9S-lipoxygenase 1, linoleate 9S-lipoxygenase 2, linoleate 9S-lipoxygenase 3, linoleate oxygen oxidoreductase, lipoxygenase, LOX, LOX1, LOX1.1, LOX1.3, LOX12, LOX13, LOX14, LOX1:Md:1c, LOX1c, LOX2, LOX3, LOX4, LOX5, LOX6, LOX7, LOX8, LOX9, LoxA, Nb-9-LOX, Osr9-LOX1, plant LOX-1, POTLX-1, r9-LOX1, seed linoleate 9S-lipoxygenase-3, StLOX1, tuberization protein, type-1 9-LOX, ZmLOX3, ZmLOX5
ECTree
1.13.11.58 linoleate 9S-lipoxygenaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.13.11.58 - linoleate 9S-lipoxygenase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(9E,11Z,14Z)-icosa-9,11,14-trienoic acid + O2
(9S,11Z,14Z)-9-hydroperoxyicosa-11,14-dienoic acid
-
good substrate
-
-
?
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2
12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2
9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2
9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
AA/Lyso-PA + O2
15-HPETE/lyso-PA + 13-HPETE/lyso-PA + 15-HPETE/lyso-PA + 11-HPETE/lyso-PA + 5-HPETE/lyso-PA
-
-
36%, 22%, 21% and 13% yield, respectively
-
?
alpha-linolenate
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate is the main product
-
?
alpha-linolenate + O2
?
comparable oxygenase activity with either linoleic acid or linolenic acid
no product determined
-
?
arachidonic acid + O2
5-HPETE + 7-HPETE + 9-HPETE
-
-
22%, 25% and 29% yield, respectively
-
?
gamma-linolenate + O2
(6Z,9S,10E,12Z)-9-hydroperoxy-6,10,12-octadecatrienoate
-
72% (6Z,9S,10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoate, with racemic 6-, 10-, and 13-gamma-hydroperoxy-(10E,12Z,15Z)-octadecatrienoates as secondary products
-
?
gamma-linolenic acid + O2
9 9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
linoleic acid + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleic acid + O2
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid
-
-
-
-
?
linolenic acid + O2
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid
-
-
-
-
?
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2
12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
-
-
-
-
?
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid + O2
12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2
9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid + O2
9,10-epoxy-11-hydroxy-cis,cis-6,12-octadecadienoic acid
-
-
-
-
?
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2
9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
-
-
-
-
?
9-hydroperoxy-trans,cis-10,12-octadecadienoic acid + O2
9,10-epoxy-11-hydroxy-cis-12-octadecenoic acid
-
-
-
-
?
alpha-linolenate + O2
(10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
-
the R/S stereoconfiguration of the product is not determined
-
?
alpha-linolenate + O2
(10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
96% (10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate and 2.1% (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
?
alpha-linolenate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
alpha-linolenate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
12-, 13-, and 16-hydroperoxy-(10E,12Z,15Z)-octadecatrienoates are minor byproducts
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
the enzyme forms exclusively (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
-
-
-
-
?
alpha-linolenate + O2
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
more than 96% of the substrate is converted to the the 9-positional hydroperoxide
-
?
alpha-linolenic acid + O2
(10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
-
-
-
?
alpha-linolenic acid + O2
(10E,12Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
-
-
-
-
?
alpha-linolenic acid + O2
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid
-
-
-
-
?
alpha-linolenic acid + O2
12-hydroperoxy-cis,trans,cis-9,13,15-octadecatrienoic acid
-
-
-
-
?
gamma-linoleic acid + O2
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
gamma-linoleic acid + O2
9-hydroperoxy-cis,trans,cis-6,10,12-octadecatrienoic acid
-
-
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade
-
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
no formation of 13-hydroperoxy-(10E,12Z)-octadecadienoate. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
no formation of 13-hydroperoxy-(10E,12Z)-octadecadienoate. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is main product. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate is main product. The R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
linoleate (abundant in membrane lipids of tubers) is preferred to linolenate as substrate
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
recombinant ZmLOX5 protein displays clear 9-LOX regiospecificity at both neutral and slightly alkaline pH
the R/S stereoconfiguration of the product is not determined
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
the main product (94%) is (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate, primarily S configuration
-
?
linoleate + O2
(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
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
the enzyme forms exclusively (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
regiospecificity of Nb-9-LOX, overview
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
low catalytic activity with complex substrates as compared to free linoleic acid. Residual relative activities lower than 1% with the substrates dilinolein, trilinolein, and 1-palmitoyl-2-linoleoyl-glycero-3-phosphocholine and with extracted lipids from malt confirm this supposition. However, LOX1 catalyzes HPODE formation from PamLinGroPCho with high regioselectivity (9-hydroperoxy-(10E,12Z)-octadecadienoate:13-hydroperoxy-(10E,12Z)-octadecadienoate) and high (9S)-hydroperoxy-(10E,12Z)-octadecadienoate stereoselectivity (S:R) (92:8)
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
the enzyme specifically forms the 9-H(p)ODE isomer by 99.5%, 97.7% of which is in S-form
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
regiospecificity of Nb-9-LOX, overview
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
comparable oxygenase activity with either linoleic acid or linolenic acid
-
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
-
-
-
?
linoleate + O2
(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
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
98% (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate, almost exclusively S stereoconfiguration. (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is a minor byproduct
-
?
linoleate + O2
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
-
9-lipoxygenase does not utilize docosadienoic acid and catalyzes eicosadienoic acid dioxygenation 20fold slower than linoleic acid dioxygenation
the enzyme specifically forms the S-stereoisomer
-
?
additional information
?
-
arachidonic acid is a poor substrate
-
-
?
additional information
?
-
arachidonic acid is a poor substrate
-
-
?
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
-
-
?
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
-
-
?
additional information
?
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
in chitosan-treated Adelostemma gracillimum seedlings 9-LOX-derived oxylipins, namely 9,10,11-trihydroxy-12-octadecenoic acid, accumulate
-
-
?
additional information
?
-
-
in chitosan-treated Adelostemma gracillimum seedlings 9-LOX-derived oxylipins, namely 9,10,11-trihydroxy-12-octadecenoic acid, accumulate
-
-
?
additional information
?
-
the enzyme converted linoleic and linolenic acids almost exclusively to their 9-hydroperoxides
-
-
?
additional information
?
-
-
the enzyme converted linoleic and linolenic acids almost exclusively to their 9-hydroperoxides
-
-
?
additional information
?
-
regio- and stereospecificity analysis of isozyme substrate specificity, recombinant LOX1:Md:1a, LOX1:Md:1c, LOX2:Md:2a, and LOX2:Md:2b isozymes show 13/9-LOX, 9-LOX, 13/9-LOX and 13-LOX activity with linoleic acid, respectively. While products of LOX1:Md:1c and LOX2:Md:2b are S-configured, LOX1:Md:1a and LOX2:Md:2a form 13(R)-hydroperoxides as major products. Oxygenation in the carbon backbone of linoleic acid occurs either at carbon atom 9 (9-LOX) or 13 (13-LOX), forming the corresponding hydroperoxy derivatives, respectively. LOX enzymes are not perfectly specific and biocatalysts that produce more than 10% of the alternative regio-isomer are called dual positional specific LOX
-
-
?
additional information
?
-
-
regio- and stereospecificity analysis of isozyme substrate specificity, recombinant LOX1:Md:1a, LOX1:Md:1c, LOX2:Md:2a, and LOX2:Md:2b isozymes show 13/9-LOX, 9-LOX, 13/9-LOX and 13-LOX activity with linoleic acid, respectively. While products of LOX1:Md:1c and LOX2:Md:2b are S-configured, LOX1:Md:1a and LOX2:Md:2a form 13(R)-hydroperoxides as major products. Oxygenation in the carbon backbone of linoleic acid occurs either at carbon atom 9 (9-LOX) or 13 (13-LOX), forming the corresponding hydroperoxy derivatives, respectively. LOX enzymes are not perfectly specific and biocatalysts that produce more than 10% of the alternative regio-isomer are called dual positional specific LOX
-
-
?
additional information
?
-
-
Nb-9-LOX possesses both 9-lipoxygenase and 13-lipoxygenase, EC 1.13.11.12, specificity, with high predominance for the 9-LOX function
-
-
?
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
-
-
?
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
-
-
?
additional information
?
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
-
low activity with arachidonate, the C20 fatty acid is converted into a mixture of racemic products
-
-
?
additional information
?
-
-
the enzyme catalyzes oxygenation at the n-12 position of C20 and C22 polyunsaturated fatty acids to form 9S- and 11S-hydroperoxy fatty acids, which are reduced to 9S- and 11S-hydroxy fatty acids by cysteine, respectively, and it catalyzes again oxygenation at the n-6 position of 11S-hydroxy fatty acids to form 9S,15S- and 11S,17S-dihydroxy fatty acids, respectively
-
-
-
