1.13.11.60: linoleate 8R-lipoxygenase

This is an abbreviated version!
For detailed information about linoleate 8R-lipoxygenase, go to the full flat file.

Word Map on EC 1.13.11.60

Reaction

linoleate
+
O2
=
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate

Synonyms

5,8-LDS, 5,8-linoleate diol synthase, 5,8-linoleate diol synthases, 7,8-diol synthase, 7,8-LDS, 7,8-linoleate diol synthase, 8(R)-dioxygenase, 8,11-hydroperoxide isomerase, 8-DOX, 8R-dioxygenase, 8R-DOX, dioxygenase-cytochrome P450, DOX-CYP, FOXB_09952, GLRG_10013, linoleate 7,8-LDS, linoleate 8,11-LDS, linoleate diol synthase, linoleic acid 8R-dioxygenase, orphan DOX-CYP, PpoA

ECTree

     1 Oxidoreductases
         1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)
             1.13.11 With incorporation of two atoms of oxygen
                1.13.11.60 linoleate 8R-lipoxygenase

Engineering

Engineering on EC 1.13.11.60 - linoleate 8R-lipoxygenase

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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C1006S
the hydroperoxide isomerase activity of 5,8-LDS mutant is abolished
C1006S/V328F
the mutant forms after reduction of hydroperoxides to alcohols, (8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid and (10R)-hydroxy-(8E,12Z)-octadecadienoic acid in the same relative amounts
C1006S/V328L
the mutant forms after reduction of hydroperoxides to alcohols, (8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid and (10R)-hydroxy-(8E,12Z)-octadecadienoic acid in the same relative amounts
C1006S/V328S
the mutant forms after reduction of hydroperoxides to alcohols, (8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid and (10R)-hydroxy-(8E,12Z)-octadecadienoic acid in the same relative amounts
N887L
-
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
N887Q
-
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main metabolite with an increased formation of 6,8- and 8,11-dihydroxylinoleate
Q890E
-
site-directed mutagenesis, the mutant retains (5S,8R)-5,8-dihydroxylinoleate as the main product, but shifts oxygenation from C-5 to C-7 and C-11 and to formation of epoxyalcohols by homolytic scission of (8R)-hydroperoxylinoleic acid
Q890L
-
site-directed mutagenesis, the mutant shows almost abolished 5,8-linoleate diol synthase activity
Y374F
mutation in the conserved sequence YRWH results in loss of linoleate 8R-lipoxygenase activity, whereas the hydroperoxide isomerase activity is retained
H1004A
mutant enzyme with abolished 8-hydroperoxide isomerase activity, whereas dioxygenase activity is still present
Y374
the mutant enzyme shows no detectable activity when incubated with (9Z,12Z)-octadeca-9,12-dienoate as a substrate. When incubated with the intermediate product (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate it is able to catalyze isomerization to (5S,8R,9Z,12Z)-5,8-dihydroperoxy-9,12-octadecadienoate
A891G
site-directed mutagenesis, the mutant converts linoleic acid to 7,8-DiHODE as major product and 8,11-DiHODE as minor product, which is the similar pattern as the wild-type enzyme
C1038S
site-directed mutagenesis, the mutant produces a low amount of 7,8-DiHODE with the accumulation of 8-HPODE
H1036A
site-directed mutagenesis, the mutant produces a low amount of 7,8-DiHODE with the accumulation of 8-HPODE
H1036A/C1038S
site-directed mutagenesis, the double mutant converts linoleic acid to only 8-HPODE
N895D
site-directed mutagenesis, the mutant produces a reduced amount of 8-HPODE, compared to wild-type, without the accumulation of DiHODE
N895L
site-directed mutagenesis, the mutant converts linoleic acid to 7,8-DiHODE as major product and 8,11-DiHODE as minor product, which is the similar pattern as the wild-type enzyme
N895Q
site-directed mutagenesis, the mutant converts linoleic acid to 7,8-DiHODE as major product and 8,11-DiHODE as minor product, which is the similar pattern as the wild-type enzyme
Q898E
site-directed mutagenesis, the mutant converts linoleic acid to 8,11-DiHODE as major product and 7,8-DiHODE as minor product
Q898L
site-directed mutagenesis, the mutant converts linoleic acid to 8,11-DiHODE as major product and 7,8-DiHODE as minor product
Y380F
site-directed mutagenesis, the mutant enzyme produces trace amount of 7,8-DiHODE without the accumulation of 8-HPODE when incubated with linoleic acid as substrate
A891G
-
site-directed mutagenesis, the mutant converts linoleic acid to 7,8-DiHODE as major product and 8,11-DiHODE as minor product, which is the similar pattern as the wild-type enzyme
0
N895D
-
site-directed mutagenesis, the mutant produces a reduced amount of 8-HPODE, compared to wild-type, without the accumulation of DiHODE
0
N895L
-
site-directed mutagenesis, the mutant converts linoleic acid to 7,8-DiHODE as major product and 8,11-DiHODE as minor product, which is the similar pattern as the wild-type enzyme
0
Y380F
-
site-directed mutagenesis, the mutant enzyme produces trace amount of 7,8-DiHODE without the accumulation of 8-HPODE when incubated with linoleic acid as substrate
0
E384A
-
mutant forms only traces of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
H203Q
weak activity
H379Q
I375A
-
mutant has virtually no dioxygenase activity
K540L
inactive mutant enzyme
K540Q
inactive mutant enzyme
K540R
inactive mutant enzyme
L334V
-
inactive mutant enzyme
N216Q
-
inactive mutant enzyme, no 8(R)-dioxygenase activity
N938D
-
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
N938L
-
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase abolishes the hydroperoxide isomerase activity of the enzyme
N938Q
-
site-directed mutagenesis, the mutation of the 7,8-linoleate diol synthase reduces the hydroperoxide isomerase activity of the enzyme
V330L
-
the wild-type enzyme forms 98% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate and 2% (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate. The V330L mutation augments the formation of (8E,10R,12Z)-10-hydroperoxy-8,12-octadecadienoate 3fold
Y329F
weak activity
Y329L
inactive mutant enzyme
Y376F
inactive mutant enzyme
Y378F
inactive mutant enzyme
Y378S
inactive mutant enzyme
Y531F
inactive mutant enzyme
H379Q
-
inactive mutant enzyme, no 8(R)-dioxygenase activity
0
N216Q
-
inactive mutant enzyme, no 8(R)-dioxygenase activity
0
additional information