1.13.11.45: linoleate 11-lipoxygenase
This is an abbreviated version!
For detailed information about linoleate 11-lipoxygenase, go to the full flat file.
Word Map on EC 1.13.11.45
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1.13.11.45
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oxylipins
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graminis
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bis-allylic
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gaeumannomyces
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suprafacial
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take-all
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antarafacial
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atlox2
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lipoxygenation
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hydroperoxy
- 1.13.11.45
- oxylipins
- graminis
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bis-allylic
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gaeumannomyces
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suprafacial
-
take-all
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antarafacial
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atlox2
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lipoxygenation
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hydroperoxy
Reaction
Synonyms
13 R -MnLOX, 13R-MnLOX, Cg-MnLOX, CspLOX2, Fo-MnLOX, linoleate dioxygenase, lipoxygenase 2, LOX-1, manganese lipoxygenase, manganese LOX, MGG_08499, Mn-LO, Mn-LOX, MnLOX, Mo-MnLOX
ECTree
1.13.11.45 linoleate 11-lipoxygenaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.13.11.45 - linoleate 11-lipoxygenase
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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
(10Z,13Z,16Z)-nonadeca-10,13,16-trienoic acid + O2
?
-
oxidation at the n-6 carbon and at the bis-allylic position n-8
-
-
?
(11Z,14Z)-eicosa-11,14-dienoic acid + O2
?
-
LC-MS analysis shows that Fo-MnLOX oxidizes (11Z,14Z)-eicosa-11,14-dienoic acid efficiently at both C-15 and C-11
-
-
?
(11Z,14Z)-eicosadienoic acid + O2
15-hydroxyperoxy-(9Z,11E)-eicosadienoic acid
-
-
-
-
?
(11Z,14Z,17Z)-eicosa-11,14,17-trienoic acid + O2
15-hydroxyperoxy-11Z,13E,17Z-eicosatrienoic acid
-
via 11-hydroperoxyoctadecadienoic acid, 13-hydroperoxyoctadecadienoic acid and 15-hydroperoxyoctadecadienoic acid
-
-
?
(13R)-hydroperoxylinolenic acid + O2
13-ketolinolenic acid + epoxyalcohols
only mutant enzyme G316A
erythro- and threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acids and one of the corresponding cis-epoxides as major products
-
?
(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoic acid + O2
(5Z,8Z,11S,12E,14Z)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid + (5Z,8Z,11Z,13E,15R)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
-
oxidation at the n-6 carbon and at the bis-allylic position n-8
-
-
?
(5Z,8Z,11Z,14Z,17Z)-docosa-5,8,11,14,17-pentaenoate + O2
?
-
oxidation at the n-6 carbon and at the bis-allylic position n-8
-
-
?
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + O2
?
-
oxidation at the n-6 carbon and at the bis-allylic position n-8
-
-
?
(9E,12Z)-octadeca-9,12-dienoic acid + O2
?
-
sLOX-1 oxidizes (9E,12Z)18:2 to 9-hydroperoxyoctadecadienoic acid in an R/S ratio of 60/40 and to 13-hydroperoxyoctadecadienoic acid
-
-
?
(9Z,11S,12Z)-11-hydroperoxyoctadeca-9,12-dienoate + O2
(9Z,11E, 13R)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
(9Z,11S,12Z)-11-hydroperoxyoctadeca-9,12-dienoate + O2
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoate
-
-
-
-
?
(9Z,12E)-octadeca-9,12-dienoic acid + O2
?
-
sLOX-1 oxidizes (9Z,12E)18:2 slowly to the 9-hydroperoxy metabolite with 10E,12E configuration as the main product (65%) and to 13-hydroperoxyoctadecadienoic acid
-
-
?
(9Z,12Z)-octadeca-9,12-dienoic acid + O2
(9S)-hydroperoxy-octadeca-10,12-dienoate
-
alpha-linoleate is converted via two intermediates, (11S)-hydroperoxy-(9Z,12Z)-octadecenoate and (13R)-hydroperoxy-(9Z,11E)-octadecadienoate, which are isomerized to the end product, probably after oxidation to peroxyl radicals, beta-fragmentation, and oxygen insertion at C-9
-
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
(10E,12E,14E)-9,16-dihydroxy-octadeca-10,12,14-trienoate
-
gamma-linoleate is oxidized at C-9, C-11, and C-13
-
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
(13R)-hydroperoxyoctadecadienoic acid
-
via bis-allylic 11S-hydroperoxy fatty acid
-
-
?
1,2-dilinoleoyl-sn-glycero-3-phosphocholine + O2
?
-
-
main products with 14% and 10%, no production of 11-hydroxyoctadecanoic acid
-
?
1-linoleoyl-2-hydroxy-phosphatidylcholine + O2
?
an excellent substrate
-
-
?
1-linoleyl-lyso-glycerophosphatidylcholine + O2
11-hydroxyoctadecanoic acid + 13-hydroxyoctadecanoic acid
-
via formation of the 13-hydroxyperoxy metabolite
-
-
?
11-(11R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
9-(9R)-hydroperoxy-octadecadienoic acid
-
slow
-
-
?
11-(11S)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
13-(13R)-hydroperoxy-(9Z,11E)-octadecadienoic acid
11-(11S)-hydroperoxy-(9Z,12Z)-octadecadienoic acid methyl ester
13-(13R)-hydroperoxy-(9Z,11E)-octadecadienoic acid methyl ester
-
-
-
-
?
11-hydroperoxyoctadecadienoic acid + O2
11,18-dihydroxy-12E,14Z,16E-eicosatrienoic acid
-
-
two diastereoisomers
-
?
alpha-linolenic acid + O2
(13R)-hydroperoxy octadecadienoic acid + 9-hydroperoxyoctadecadienoic acid
-
-
-
-
?
alpha-linolenic acid + O2
(9Z,11E,15Z)-(13)-hydroperoxyoctadecatrienoic acid
-
-
-
-
?
gamma-linolenic acid + O2
(6Z,9Z,11E)-(13)-hydroperoxyoctadecatrienoic acid + (6Z,9Z,12Z)-(11)-hydroperoxyoctadecatrienoic acid
-
-
-
-
?
linoleate + O2
(9Z,11S,12Z)-11-hydroperoxyoctadeca-9,12-dienoate
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13R)-hydroperoxyoctadecadienoic acid + (9Z,12Z)-(11S)-hydroperoxyoctadecadienoic acid
-
-
-
ir
linolenate + O2
(11R)-hydroperoxyoctadecadienoic acid + 13S-hydroperoxyoctadecadienoic acid + 9(S/R)-hydroperoxyoctadecadienoic acid
-
Fo-MnLOX, with support of Ser348, binds linoleic acid so that the pro R rather than the pro S hydrogen at C-11 interacts with the metal center, but retains the suprafacial oxygenation mechanism observed in other MnLOXs
-
-
?
linolenate + O2
(11S)-hydroperoxyoctadecadienoic acid + (13R)-hydroperoxyoctadecadienoic acid + (9S)-hydroperoxyoctadecadienoic acid
-
-
-
-
?
linolenic acid + O2
11-(11S)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
-
-
-
-
?
(11Z,14Z,17Z)-eicosa-11,14,17-trienoic acid + O2
?
-
oxidation at the n-6 carbon and at the bis-allylic position n-8
-
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
?
-
oxidation at the bis-allylic n-5 carbon and at positions n-3, n-7, and n-6
-
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2
?
-
oxidation at the n-3 position
-
-
?
11-(11S)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
13-(13R)-hydroperoxy-(9Z,11E)-octadecadienoic acid
-
47% the rate of conversion of linolenic acid
-
-
?
11-(11S)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
13-(13R)-hydroperoxy-(9Z,11E)-octadecadienoic acid
-
rapid
-
-
?
linoleate + O2
(9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
-
-
-
-
?
linoleate + O2
(9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
-
via bis-allylic 11S-hydroperoxy fatty acid
-
-
?
linoleate + O2
(9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
linoleate + O2
(9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
-
-
-
?
linoleate + O2
(9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
analysis of substrate conformation and environment, overview
-
-
?
linoleic acid + O2
(9Z,11E)-(13R)-hydroperoxyoctadecadienoic acid
-
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13R)-hydroperoxyoctadecadienoic acid
-
-
-
?
linoleic acid + O2
(9Z,11E)-(13R)-hydroperoxyoctadecadienoic acid
-
-
-
-
?
lyso-phosphatidylcholine + O2
?
-
substrate from soybean
-
-
?
additional information
?
-
-
the 11-hydroperoxide does not undergo the rapid beta-fragmentation observed with 13R-MnLOX. Oxidation of [11S-2H]-linoleic acid by Cg-MnLOX is accompanied by loss of deuterium and a large kinetic isotope effect. Substrate specificity, overview
-
-
?
additional information
?
-
-
the 11-hydroperoxide does not undergo the rapid beta-fragmentation observed with 13R-MnLOX. No significant oxidation of (7Z,10Z,13Z)-hexadeca-7,10,13-trienoic acid, (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid, and arachidonic acid. The alpha-linolenic acid, which forms 11R-hydro(pero)xy-9Z,12Z,15Z-octadecatrienoic acid as a main metabolite, is oxidized to 9- and 13R-hydro(pero)xy-9Z,11E,15Z-octadecatrienoic acid at a much lower rate compared with linoleic acid, (11Z,14Z)-eicosa-11,14-dienoic acid, and (11Z,14Z,17Z)-eicosa-11,14,17-trienoic acid. Substrate specificity, overview
-
-
?
additional information
?
-
-
Mn-LO likely binds fatty acids tail-first and oxygenates many C16, C18, C20, and C22 fatty acids to significant amounts of bis-allylic hydroperoxides. Unsaturated C16-C22 fatty acids, other than 18:3n-3, 18:2n-6, or 17:3n-3, are poor substrates, possibly because of ineffective enzyme activation through Mn2+ to Mn3+ by the produced hydroperoxides, substrate specificities of wild-type and mutant enzymes, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes the rearrangement of bis-allylic S-hydroxyperoxides to allylic R-hydroperoxides, and the oxygenation of 18:2n-6 by suprafacial hydrogen abstraction at C11 and O2 insertion at the bis-allylic position C11 and, with double bond migation, at the allylic position C13, overview, 20:4n-6 is a poor substrate, substrate specificities of wild-type and mutant enzymes, overview
-
-
?
additional information
?
-
-
13R-MnLOX forms (11S)-hydroperoxyoctadecadienoic acid and (11R)-hydroperoxyoctadecatrienoic acid as intermediates during the linear phase of oxidation and the (13R)-hydroperoxides as main end products
-
-
?
additional information
?
-
-
cf. EC 1.13.11.58, LC- and GC-MS analysis product analysis, overview
-
-
?
additional information
?
-
-
oxidation of 18:1 n-6 is performed by 13R-MnLOX
-
-
?
additional information
?
-
-
(9Z,12E)18:2 is not oxidized at a detectable rate. sLOX-1 oxidizes (9E,12Z)18:2 more efficiently than (9Z,12E)18:2
-
-
?
additional information
?
-
the enzyme can also convert linoleate to (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and (9Z,11E)-(13R)-13-hydroperoxyoctadeca-9,11-dienoate, cf. linoleate 9S-lipoxygenase/EC 1.13.11.58 and linoleate 13R-lipoxygenase. Oxygen consumption monitoring
-
-
?
additional information
?
-
-
the enzyme can also convert linoleate to (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate and (9Z,11E)-(13R)-13-hydroperoxyoctadeca-9,11-dienoate, cf. linoleate 9S-lipoxygenase/EC 1.13.11.58 and linoleate 13R-lipoxygenase. Oxygen consumption monitoring
-
-
?
