1.13.11.61: linolenate 9R-lipoxygenase
This is an abbreviated version!
For detailed information about linolenate 9R-lipoxygenase, go to the full flat file.
Word Map on EC 1.13.11.61
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1.13.11.61
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linoleic
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diol
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ala
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dioxygenation
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lipoxygenases
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polyunsaturated
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nostoc
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cyanobacterial
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regio
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hydroperoxides
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aspergilli
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homolytic
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allene
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terreus
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stereochemistry
- 1.13.11.61
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linoleic
- diol
- ala
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dioxygenation
- lipoxygenases
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polyunsaturated
- nostoc
-
cyanobacterial
-
regio
- hydroperoxides
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aspergilli
-
homolytic
-
allene
- terreus
-
stereochemistry
Reaction
Synonyms
(9R)-LOX, 11R-LOX, 9R-lipoxygenase, 9R-LOX, ARA 11RLOX, arachidonate 11R-lipoxygenase, CspLOX2, LA 9RLOX, linoleate 11R-lipoxygenase, linoleate 9R-dioxygenase, lipoxygenase 2, NspLOX
ECTree
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Substrates Products
Substrates Products on EC 1.13.11.61 - linolenate 9R-lipoxygenase
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REACTION DIAGRAM
alpha-linolenic acid + O2
(9Z,12E,15Z)-9R-hydroxy-9,12,15-octadecatrienoic acid
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?
gamma-linolenic acid + O2
(6Z,10E,12Z)-9R-hydroxy-6,10,12-octadecatrienoic acid
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-
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-
?
linoleic acid + O2
(10E,12Z)-9R-hydroxy-10,12-octadecadienoic acid
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-
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?
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
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-
?
alpha-linolenate + O2
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
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-
?
alpha-linolenate + O2
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Preferred substrate
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-
?
alpha-linolenate + O2
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
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-
?
alpha-linolenate + O2
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Preferred substrate
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-
?
alpha-linolenate + O2
(9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
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i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
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-
?
(9R,10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid
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-
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?
alpha-linolenic acid + O2
(9R,10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid
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-
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?
(9R,10E,12Z,15Z)-9-hydroxy-octadeca-10,12,15-trienoic acid
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optimal reaction conditions are pH 8.5, 15°C, 5% v/v acetone, 0.2% w/v Tween 80, 40 g/l alpha-linolenic acid, and 1 g/l enzyme, assay method optimization
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-
?
alpha-linolenic acid + O2
(9R,10E,12Z,15Z)-9-hydroxy-octadeca-10,12,15-trienoic acid
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optimal reaction conditions are pH 8.5, 15°C, 5% v/v acetone, 0.2% w/v Tween 80, 40 g/l alpha-linolenic acid, and 1 g/l enzyme, assay method optimization
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-
?
(6Z,9R,10E,12Z)-9-hydroxy-octadeca-6,10,12-trienoic acid
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-
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?
gamma-linolenic acid + O2
(6Z,9R,10E,12Z)-9-hydroxy-octadeca-6,10,12-trienoic acid
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-
-
-
?
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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i.e. (9Z,12Z)-octadeca-9,12-dienoate. (9R,10EZ,12Z)-9-Hydroperoxy-10,12-octadecadienoate is formed by antarafacial hydrogen abstraction and oxygenation
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-
?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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i.e. (9Z,12Z)-octadeca-9,12-dienoate
configuration of the 9-hydroperoxide is primarily R (93%). (13S)-Hydroperoxy octadecadienoic acid is detected in small amounts as by-product
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?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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the enzyme is involved in oxylipin biosyntesis
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-
?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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i.e. (9Z,12Z)-octadeca-9,12-dienoate, the C-terminal portion of NspLOX is identified as a linoleate linoleate (9R)-lipoxygenase. 42% of the activity with alpha-linolenic acid
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?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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the enzyme is involved in oxylipin biosyntesis
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-
?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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i.e. (9Z,12Z)-octadeca-9,12-dienoate, the C-terminal portion of NspLOX is identified as a linoleate linoleate (9R)-lipoxygenase. 42% of the activity with alpha-linolenic acid
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-
?
linoleate + O2
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
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i.e. (9Z,12Z)-octadeca-9,12-dienoate
configuration of the 9-hydroperoxide is primarily R (93%). (13S)-Hydroperoxy octadecadienoic acid is detected in small amounts as by-product
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?
(9Z,11R,12Z)-11-hydroperoxyoctadeca-9,12-dienoate
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?
linoleate + O2
(9Z,11R,12Z)-11-hydroperoxyoctadeca-9,12-dienoate
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analysis of substrate conformation and environment, overview
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?
linoleic acid + O2
(9R,10E,12Z)-9-hydroxy-octadeca-10,12-dienoic acid
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?
?
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selective production of 9R-hydroxy-10E,12Z,15Z-octadecatrienoic acid from alpha-linolenic acid in Perilla seed oil hydrolyzate by the enzyme from Nostoc sp. strain SAG 25.82, heterologously expressed in Escherichia coli. The specific activity of the enzyme followed the descending order linoleic acid > alpha-linolenic acid > gamma-linolenic acid. Product determination by LC-MS/MS analysis
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?
additional information
?
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selective production of 9R-hydroxy-10E,12Z,15Z-octadecatrienoic acid from alpha-linolenic acid in Perilla seed oil hydrolyzate by the enzyme from Nostoc sp. strain SAG 25.82, heterologously expressed in Escherichia coli. The specific activity of the enzyme followed the descending order linoleic acid > alpha-linolenic acid > gamma-linolenic acid. Product determination by LC-MS/MS analysis
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?
additional information
?
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CspLOX1 only produces conjugated hydroperoxyoctadeca-9,12-dienoate in a way that it imitates CspLOX2 and forms 11-hydroperoxyoctadeca-9,12-dienoate
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?