5.4.4.5: 9,12-octadecadienoate 8-hydroperoxide 8R-isomerase
This is an abbreviated version!
For detailed information about 9,12-octadecadienoate 8-hydroperoxide 8R-isomerase, go to the full flat file.
Reaction
Synonyms
5,8-LDS, 5,8-linoleate diol synthase, PpoA
ECTree
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Substrates Products
Substrates Products on EC 5.4.4.5 - 9,12-octadecadienoate 8-hydroperoxide 8R-isomerase
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REACTION DIAGRAM
(8R,9Z,12Z)-8-hydroperoxy-10,12-octadecadienoate
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate
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(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate
(8R,9Z,12Z)-9-hydroperoxy-10,12-octadecadienoate
(5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate
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(5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate
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(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate
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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 hydrogens at C-5 of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate, respectively, followed by suprafacial oxygenation
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(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate
the enzyme is involved in the regulation of the life cycle of Aspergillus nidulans. Synthesis of the psi factor (8R,9E,12Z)-8-hydroperoxy-9,12-octadecadienoate, that influences the development of the asexual conidiophores and sexual cleistothecia
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(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate
(5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate
the N-terminal heme peroxidase domain is responsible for the dioxygenase reaction as the first step of the PpoA reaction, i.e. oxidation of linoleic acid to (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate as an intermediate product. The C-terminal P450 domain catalyzes the second reaction step, the isomerization of (8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate to (5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate, and is therefore termed the 8-hydroperoxide isomerase P450 domain
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