EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
1.13.11.60 | linoleate + O2 |
i.e. (9Z,12Z)-octadeca-9,12-dienoate |
Aspergillus clavatus |
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate |
- |
? |
1.13.11.60 | linoleate + O2 |
i.e. (9Z,12Z)-octadeca-9,12-dienoate. Mechanism of biosynthesis: the enzyme oxidizes linoleic acid to (8R)-hydroperoxylinoleic acid and to (5S,8R)-dihydroxylinoleic acids as major products. This occurs by abstraction of the pro-S hydrogen at C-8 and antarafacial dioxygenation at C-8 or at C-10 with double bond migration. (8R,9Z,12Z)-8-Hydroperoxy-9,12-octadecadienoate is then isomerized to (5S,8R,9Z,12Z)-5,8-dihydroperoxy-9,12-octadecadienoate by abstraction of the pro-S hydrogen at C-5 of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate, respectively, followed by suprafacial oxygenation |
Aspergillus clavatus |
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate |
- |
? |
1.13.11.60 | (11Z)-icosa-11-enoate + O2 |
- |
Aspergillus fumigatus |
? |
- |
? |
1.13.11.60 | (11Z,14Z)-icosa-11,14-dienoic acid + O2 |
- |
Aspergillus fumigatus |
? |
- |
? |
1.13.11.60 | alpha-linolenate + O2 |
- |
Aspergillus fumigatus |
? |
- |
? |
1.13.11.60 | elaidate + O2 |
- |
Aspergillus fumigatus |
? |
- |
? |
1.13.11.60 | linoleate + O2 |
i.e. (9Z,12Z)-octadeca-9,12-dienoate |
Aspergillus fumigatus |
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate |
- |
? |
1.13.11.60 | linoleate + O2 |
- |
Aspergillus fumigatus |
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate |
- |
? |
1.13.11.60 | linoleate + O2 |
all-cis-9,12-octadecadienoic acid |
Aspergillus fumigatus |
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate |
- |
? |
1.13.11.60 | more |
the bifunctional enzyme forms 5S,8S-dihydroxylinoleic acid from (8R)-hydroperoxylinoleic acid by intramolecular oxygen transfer. Linoleate diol synthases are fungal dioxygenase-cytochrome P450 fusion enzymes. P450 hydroxylases usually contain an acid-alcohol pair in the I-helices for the heterolytic scission of O2 and formation of compound I, i.e. Por+-Fe(IV)=O, and water. The function of the acid-alcohol pair appears to be replaced by a different amide residue, Gln890 of 5,8-LDS, for heterolysis of (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate to generate compound I |
Aspergillus fumigatus |
? |
- |
? |