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Literature summary extracted from
- Leucine/valine residues direct oxygenation of linoleic acid by (10R)- and (8R)-dioxygenases: expression and site-directed mutagenesis oF (10R)-dioxygenase with epoxyalcohol synthase activity (2009), J. Biol. Chem., 284, 13755-13765.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.13.11.60 | expression in SF21 cells | Gaeumannomyces graminis |
| 1.13.11.62 | expression in SF21 cells | Aspergillus fumigatus |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.13.11.60 | E384A | mutant forms only traces of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | Gaeumannomyces graminis |
| 1.13.11.60 | I375A | mutant has virtually no dioxygenase activity | Gaeumannomyces graminis |
| 1.13.11.60 | L334V | inactive mutant enzyme | Gaeumannomyces graminis |
| 1.13.11.60 | 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 | Gaeumannomyces graminis |
| 1.13.11.62 | L306A | the relative biosynthesis of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate compared to (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate is slightly lowered | Aspergillus fumigatus |
| 1.13.11.62 | L306V | the relative biosynthesis of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate compared to (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate is slightly lowered | Aspergillus fumigatus |
| 1.13.11.62 | L384A | the relative amount of (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate (8-HODE/(10-HODE + 8-HODE)) is 10.4% for the recombinant wild-type enzyme and 53.7% for the mutant enzyme. The L384A mutant changes the stereochemistry at C-8 and C-10. L384A forms the R and S enantiomers of 8-HODE and 10-HODE in a ratio of 3:2, whereas native and recombinant 10R-DOX form both products with 95% R configuration | Aspergillus fumigatus |
| 1.13.11.62 | L384F | increases the relative biosynthesis of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate compared to (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate to 48% (the wild-type enzyme forms 90% (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate and 10% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate) | Aspergillus fumigatus |
| 1.13.11.62 | L384M | increases the relative biosynthesis of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate compared to (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate with 3-4% units | Aspergillus fumigatus |
| 1.13.11.62 | L384V | the relative amount of (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate (8-HODE/(10-HODE + 8-HODE)) is 10.4% for the recombinant wild-type enzyme and 22.1% for the mutant enzyme | Aspergillus fumigatus |
| 1.13.11.62 | V388F | the wild-type enzyme forms 90% (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate and 10% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate. The mutation increases the formation of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate to 36% | Aspergillus fumigatus |
| 1.13.11.62 | V388L | the wild-type enzyme forms 90% (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate and 10% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate. The mutation increases the formation of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate to 16% | Aspergillus fumigatus |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.13.11.62 | 0.05 | - |
linoleate | pH and temperature not specified in the publication | Aspergillus fumigatus |  |
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 | i.e. (9Z,12Z)-octadeca-9,12-dienoate | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.62 | linoleate + O2 | Aspergillus fumigatus | i.e. (9Z,12Z)-octadeca-9,12-dienoate. The enzyme is involved in biosynthesis of oxylipins, which affect sporulation, development, and pathogenicity of Aspergilli | (8E,10R,12Z)-10-hydroperoxy-8,12-octadecadienoate | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.13.11.60 | Gaeumannomyces graminis | - |
- |
- |
| 1.13.11.62 | Aspergillus fumigatus | Q4WY82 | - |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.13.11.60 | linoleate + O2 | i.e. (9Z,12Z)-octadeca-9,12-dienoate | Gaeumannomyces graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | - |
? | |
| 1.13.11.60 | linoleate + O2 | i.e. (9Z,12Z)-octadeca-9,12-dienoate | Gaeumannomyces graminis | (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate | the wild-type enzyme forms 98% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate and 2% (10R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate. The V330L mutation augments the formation of (10R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate 3fold | ? | |
| 1.13.11.62 | alpha-linolenate + O2 | i.e. (9Z,12Z,15Z)-octadeca-9,12,15-trienoate | Aspergillus fumigatus | (8E,10R,12Z,15Z)-10-hydroperoxy-8,12,15-octadecatrienoate | - |
? | |
| 1.13.11.62 | linoleate + O2 | i.e. (9Z,12Z)-octadeca-9,12-dienoate. The enzyme is involved in biosynthesis of oxylipins, which affect sporulation, development, and pathogenicity of Aspergilli | Aspergillus fumigatus | (8E,10R,12Z)-10-hydroperoxy-8,12-octadecadienoate | - |
? | |
| 1.13.11.62 | linoleate + O2 | i.e. (9Z,12Z)-octadeca-9,12-dienoate. The wild-type enzyme forms 90% (8E,10R,12Z)-10-hydroperoxy-9,12-octadecadienoate, 10% (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate and small amounts of 12S(13R)-epoxy-(10R)-hydroxy-(8E)-octadecenoic acid | Aspergillus fumigatus | (8E,10R,12Z)-10-hydroperoxy-8,12-octadecadienoate | - |
? | |
| 1.13.11.62 | additional information | recombinant enzyme lacks hydroperoxide isomerase activity, but shows low epoxyalcohol synthase activity with biosynthesis of a novel oxylipin, 12S(13R)-epoxy-(10R)-hydroxy-18:1. The enzyme oxygenates 20:4n-6 (all-cis-5,8,11,14-eicosatetraenoic acid) i.e. by hydrogen abstraction at both C-13 and C-10 with formation of two nonconjugated and four cis-trans-conjugated hydroperoxyeicosatetraenoic acid | Aspergillus fumigatus | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.13.11.60 | 7,8-LDS | bifunctional enzyme | Gaeumannomyces graminis |
| 1.13.11.60 | 7,8-linoleate diol synthase | bifunctional enzyme | Gaeumannomyces graminis |
| 1.13.11.62 | (10R)-dioxygenase | - |
Aspergillus fumigatus |
| 1.13.11.62 | 10R-DOX | - |
Aspergillus fumigatus |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.13.11.62 | physiological function | the enzyme is involved in biosynthesis of oxylipins, which affect sporulation, development, and pathogenicity of Aspergilli | Aspergillus fumigatus |
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