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(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
conversion of (8R)-hydroperoxylinoleic acid into (7S,8S)-dihydroxylinoleic acid by stereospecific elimination of the pro-S hydrogen from C-7 and intramolecular suprafacial insertion of oxygen at C-7
-
-
?
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
(9Z)-8-hydroperoxyoctadeca-9-enoic acid
(9Z)-7,8-dihydroxyoctadeca-9-enoic acid
isomerase reaction of the C-terminal domain
-
-
r
(9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoic acid
(9Z,12Z,15Z)-7,8-dihydroxyoctadeca-9,12,15-trienoic acid
isomerase reaction of the C-terminal domain
-
-
r
alpha-linolenate + O2
(9Z,12Z,15Z)-7,8-dihydroperoxyoctadeca-9,12,15-trienoic acid
linoleate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
via (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate, whole enzyme reaction, best substrate
-
-
r
oleate + O2
(9Z)-7,8-dihydroxyoctadeca-9-enoic acid
palmitoleate + O2
(9Z)-5,8-dihydroxyhexadeca-9-enoic acid
via (9Z)-8-dihydroperoxyhexadeca-9-enoate
-
-
?
additional information
?
-
(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
bifunctional enzyme with linoleic acid (8R)-dioxygenase and hydroperoxide isomerase activities. The enzyme abstracts the 8-pro-S hydrogen from linoleic acid, which is followed by antarafacial insertion of molecular oxygen at C-8 to generate 8R-hydroperoxylinoleate. The latter is then isomerized to (7S,8S,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate by elimination of the 7-pro-S hydrogen and intramolecular suprafacial insertion of an oxygen atom from the hydroperoxide group
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
bifunctional enzyme with linoleic acid 8R-dioxygenase and hydroperoxide isomerase activities. The enzyme abstracts the 8-pro-S hydrogen from linoleic acid, which is followed by antarafacial insertion of molecular oxygen at C-8 to generate 8R-hydroperoxylinoleate. The latter is then isomerized to (7S,8S,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate by elimination of the 7-pro-S hydrogen and intramolecular suprafacial insertion of an oxygen atom from the hydroperoxide group
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
expression in Pichia pastoris changes the position and stereospecificity of a hydroperoxide isomerase (the recombinant enzyme forms 5,8(R)-dihydroxylinoleic acid (60% 5S) and 8(R),13-dihydroxyoctadeca-(9E,11E)-dienoic acid) possibly due to N- or O-linked mannosides in the vicinity of the heme group, whereas the (8R)-dioxygenase activity is identical with native 7,8-linoleate diol synthase
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
expression in Pichia pastoris changes the position and stereospecificity of a hydroperoxide isomerase (the recombinant enzyme forms 5,8(R)-dihydroxylinoleic acid (60% 5S) and 8(R),13-dihydroxyoctadeca-(9E,11E)-dienoic acid) possibly due to N- or O-linked mannosides in the vicinity of the heme group, whereas the (8R)-dioxygenase activity is identical with native 7,8-linoleate diol synthase
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
bifunctional enzyme with linoleic acid (8R)-dioxygenase and hydroperoxide isomerase activities. The enzyme abstracts the 8-pro-S hydrogen from linoleic acid, which is followed by antarafacial insertion of molecular oxygen at C-8 to generate 8R-hydroperoxylinoleate. The latter is then isomerized to (7S,8S,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate by elimination of the 7-pro-S hydrogen and intramolecular suprafacial insertion of an oxygen atom from the hydroperoxide group
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
r
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
isomerase reaction of the C-terminal domain
-
-
r
alpha-linolenate + O2
(9Z,12Z,15Z)-7,8-dihydroperoxyoctadeca-9,12,15-trienoic acid
via (9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoic acid, best substrate with respect to whole enzyme activity
-
-
?
alpha-linolenate + O2
(9Z,12Z,15Z)-7,8-dihydroperoxyoctadeca-9,12,15-trienoic acid
via (9Z,12Z,15Z)-8-hydroperoxyoctadeca-9,12,15-trienoic acid, whole enzyme reaction
-
-
?
oleate + O2
(9Z)-7,8-dihydroxyoctadeca-9-enoic acid
via (9Z)-8-hydroperoxyoctadeca-9-enoic acid
-
-
?
oleate + O2
(9Z)-7,8-dihydroxyoctadeca-9-enoic acid
via (9Z)-8-hydroperoxyoctadeca-9-enoic acid, whole enzyme reaction
-
-
?
additional information
?
-
the bifunctional enzyme converts linoleic acid to a product, identified as (9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy. The specific activity and catalytic efficiency (kcat/Km) of 7,8-diol synthase for the conversion of fatty acid to dihydroxy fatty acid follows the descending order linoleic acid, alpha-linolenic acid, and oleic acid, indicating that the enzyme is a 7,8-linoleate diol synthase (7,8-LDS). The reaction via (9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoic acid (8-HPODE) as an intermediate and the accumulation of 8-HPODE is due to a higher 8-dioxygenase activity in the N-terminal domain than hydroperoxide isomerase activity in the C-terminal domain, EC 5.4.4.6. 8-HPODE is subsequently isomerized to (7S,8S,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) or (5S,8R,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (5,8-DiHODE) by the C-terminal hydroperoxide isomerase domain of diol synthase
-
-
?
additional information
?
-
the bifunctional enzyme converts linoleic acid to a product, identified as (9Z,12Z)7,8-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy. The specific activity and catalytic efficiency (kcat/Km) of 7,8-diol synthase for the conversion of fatty acid to dihydroxy fatty acid follows the descending order linoleic acid, alpha-linolenic acid, oleic acid, and palmitoleic acid, indicating that the enzyme is a 7,8-linoleate diol synthase (7,8-LDS). Substrate specificity, overview. The reaction via 8-hydroperoxy-9,12(Z,Z)-octadecadienoic acid (8-HPODE) as an intermediate and the accumulation of 8-HPODE is due to a higher 8-dioxygenase activity in the N-terminal domain than hydroperoxide isomerase activity in the C-terminal domain, EC 5.4.4.6. 8-HPODE is subsequently isomerized to (7S,8S,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (7,8-DiHODE) or (5S,8R,9Z,12Z)-dihydroxyoctadeca-9,12-dienoic acid (5,8-DiHODE) by the C-terminal hydroperoxide isomerase domain of diol synthase. No activity with conjugated linoleic acid, docosapentaenoic acid, and docosahexaenoic acid, and no isomerase activity and no whole enzyme acitivity, but dioxygenase activity with eicosenoic acid, eicosadienoic acid, dihomo-gamma-linolenic acid, and arachidonic acid
-
-
?
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(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
r
(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
?
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate
-
-
-
-
?
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Su, C.; Sahlin, M.; Oliw, E.H.
A protein radical and ferryl intermediates are generated by linoleate diol synthase, a ferric hemeprotein with dioxygenase and hydroperoxide isomerase activities
J. Biol. Chem.
273
20744-20751
1998
Gaeumannomyces graminis, Gaeumannomyces graminis (Q9UUS2), Gaeumannomyces graminis var. graminis, Gaeumannomyces graminis var. graminis (Q9UUS2)
brenda
Brodowsky, I.D.; Hamberg, M.; Oliw, E.H.
A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. Biosynthesis of (8R)-Hydroxylinoleic acid and (7S,8S)-dihydroxylinoleic acid from (8R)-Hydroperoxylinoleic acid
J. Biol. Chem.
267
14738-14745
1992
Gaeumannomyces graminis
brenda
Hrnsten, L.; Su, C.; Osbourn, A.E.; Garosi, P.; Hellman, U.; Wernstedt, C.; Oliw, E.H.
Cloning of linoleate diol synthase reveals homology with prostaglandin H synthase
J. Biol. Chem.
274
28219-28224
1999
Gaeumannomyces graminis (Q9UUS2)
brenda
Brodowsky, I.D.; Hamberg, M.; Oliw, E.H.
BW A4C and other hydroxamic acids are potent inhibitors of linoleic acid 8R-dioxygenase of the fungus Gaeumannomyces graminis
Eur. J. Pharmacol.
254
43-47
1994
Gaeumannomyces graminis
brenda
Su, C.; Brodowsky, I.D.; Oliw, E.H.
Studies on linoleic acid 8R-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis
Lipids
30
43-50
1995
Gaeumannomyces graminis
brenda
Hamberg, M.; Zhang, L.Y.; Brodowsky, I.D.; Oliw, E.H.
Sequential oxygenation of linoleic acid in the fungus Gaeumannomyces graminis: Stereochemistry of dioxygenase and hydroperoxide isomerase reactions
Arch. Biochem. Biophys.
309
77-80
1994
Gaeumannomyces graminis, Gaeumannomyces graminis var.graminis
brenda
Oliw, E.H.; Su, C.; Sahlin, M.
Catalytic properties of linoleate diol synthase of the fungus Gaeumannomyces graminis: A comparison with PGH synthases
Adv. Exp. Med. Biol.
469
679-685
1999
Gaeumannomyces graminis
brenda
Garscha, U.; Oliw, E.
Pichia expression and mutagenesis of 7,8-linoleate diol synthase change the dioxygenase and hydroperoxide isomerase
Biochem. Biophys. Res. Commun.
373
579-583
2008
Gaeumannomyces graminis, Gaeumannomyces graminis (Q9UUS2), Gaeumannomyces graminis var. avenae, Gaeumannomyces graminis var. avenae (Q9UUS2)
brenda
Garscha, U.; Oliw, E.H.
Critical amino acids for the 8(R)-dioxygenase activity of linoleate diol synthase. A comparison with cyclooxygenases
FEBS Lett.
582
3547-3551
2008
Gaeumannomyces graminis (Q9UUS2)
brenda
Seo, M.J.; Shin, K.C.; An, J.U.; Kang, W.R.; Ko, Y.J.; Oh, D.K.
Characterization of a recombinant 7,8-linoleate diol synthase from Glomerella cingulate
Appl. Microbiol. Biotechnol.
100
3087-3099
2016
Colletotrichum gloeosporioides (A0A0S2SWE4), Colletotrichum gloeosporioides KACC 40961 (A0A0S2SWE4)
brenda
Seo, M.J.; Kang, W.R.; Shin, K.C.; Oh, D.K.
Production of 7,8-dihydroxy unsaturated fatty acids from plant oils by whole recombinant cells expressing 7,8-linoleate diol synthase from Glomerella cingulata
J. Agric. Food Chem.
64
8555-8562
2016
Colletotrichum gloeosporioides (A0A0S2SWE4), Colletotrichum gloeosporioides KACC 40961 (A0A0S2SWE4)
brenda