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Literature summary extracted from
- A protein radical and ferryl intermediates are generated by linoleate diol synthase, a ferric hemeprotein with dioxygenase and hydroperoxide isomerase activities (1998), J. Biol. Chem., 273, 20744-20751.
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.13.11.60 | additional information | catalysis declines due to suicide inactivation; catalysis declines due to suicide inactivation. Following column chromatography, e.g. ion exchange or zinc-affinity chromatography, hydroperoxide isomerase activity is often decreased and sometimes even undetectable by TLC, whereas 8-dioxygenase activity is always present. However, storage of the enzyme for a few days on ice often restores the hydroperoxide isomerase and appeares to increase the 7,8-linoleate diol synthase activity as well | Gaeumannomyces graminis | |
| 5.4.4.6 | additional information | catalysis declines due to suicide inactivation; catalysis declines due to suicide inactivation. Following column chromatography, e.g. ion exchange or zinc-affinity chromatography, hydroperoxide isomerase activity is often decreased and sometimes even undetectable by TLC, whereas 8-dioxygenase activity is always present. However, storage of the enzyme for a few days on ice often restores the hydroperoxide isomerase and appeares to increase the LDS activity as well | Gaeumannomyces graminis |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.60 | linoleate + O2 | Gaeumannomyces graminis | - |
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? |  |
| 1.13.11.60 | linoleate + O2 | Gaeumannomyces graminis var. graminis | - |
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | Gaeumannomyces graminis | - |
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | Gaeumannomyces graminis var. graminis | - |
(7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.13.11.60 | Gaeumannomyces graminis | - |
- |
- |
| 1.13.11.60 | Gaeumannomyces graminis | Q9UUS2 | - |
- |
| 1.13.11.60 | Gaeumannomyces graminis var. graminis | - |
- |
- |
| 1.13.11.60 | Gaeumannomyces graminis var. graminis | Q9UUS2 | - |
- |
| 4.2.1.92 | Gaeumannomyces graminis | - |
enzyme additionally has dioxygenase activity | - |
| 5.4.4.6 | Gaeumannomyces graminis | - |
- |
- |
| 5.4.4.6 | Gaeumannomyces graminis | Q9UUS2 | - |
- |
| 5.4.4.6 | Gaeumannomyces graminis var. graminis | - |
- |
- |
| 5.4.4.6 | Gaeumannomyces graminis var. graminis | Q9UUS2 | - |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.13.11.60 | - |
Gaeumannomyces graminis |
| 5.4.4.6 | - |
Gaeumannomyces graminis |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 4.2.1.92 | (9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O | mechanism | Gaeumannomyces graminis |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.13.11.60 | mycelium | - |
Gaeumannomyces graminis | - |
| 5.4.4.6 | mycelium | - |
Gaeumannomyces graminis | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.60 | linoleate + O2 | - |
Gaeumannomyces graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | 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 | Gaeumannomyces graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | 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 | Gaeumannomyces graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | - |
Gaeumannomyces graminis var. graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | 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 | Gaeumannomyces graminis var. graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | 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 | Gaeumannomyces graminis var. graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 4.2.1.92 | (8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid | - |
Gaeumannomyces graminis | (7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O | - |
? | |
| 4.2.1.92 | (8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid | - |
Gaeumannomyces graminis var. graminis | (7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
Gaeumannomyces graminis | (7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-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 | Gaeumannomyces graminis | (7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-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 | Gaeumannomyces graminis | (7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
Gaeumannomyces graminis var. graminis | (7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
| 5.4.4.6 | (8R,9Z,12Z)-8-hydroperoxy-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 | Gaeumannomyces graminis var. graminis | (7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate | - |
? | |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.13.11.60 | heme | ferric hemeprotein | Gaeumannomyces graminis | |
| 4.2.1.92 | heme | ferric heme iron | Gaeumannomyces graminis | |
| 5.4.4.6 | heme | ferric hemeprotein | Gaeumannomyces graminis | |
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