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http://hdl.handle.net/2445/125188
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DC Field | Value | Language |
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dc.contributor.author | Oliw, Ernst H. | - |
dc.contributor.author | Aragó Belenguer, Marc | - |
dc.contributor.author | Chen, Yang | - |
dc.contributor.author | Jernerén, Fredrik | - |
dc.date.accessioned | 2018-10-09T11:53:41Z | - |
dc.date.available | 2018-10-09T11:53:41Z | - |
dc.date.issued | 2016-08 | - |
dc.identifier.issn | 0022-2275 | - |
dc.identifier.uri | http://hdl.handle.net/2445/125188 | - |
dc.description.abstract | Linoleate dioxygenase-cytochrome P450 (DOX-CYP) fusion enzymes are common in pathogenic fungi. The DOX domains form hydroperoxy metabolites of 18:2n-6, which can be transformed by the CYP domains to 1,2- or 1,4-diols, epoxy alcohols, or to allene oxides. We have characterized two novel allene oxide synthases (AOSs), namely, recombinant 8R-DOX-AOS of Coccidioides immitis (causing valley fever) and 8S-DOX-AOS of Zymoseptoria tritici (causing septoria tritici blotch of wheat). The 8R-DOX-AOS oxidized 18:2n-6 sequentially to 8R-hydroperoxy-9Z,12Z-octadecadienoic acid (8R-HPODE) and to an allene oxide, 8R(9)-epoxy-9,12Z-octadecadienoic acid, as judged from the accumulation of the α-ketol, 8S-hydroxy-9-oxo-12Z-octadecenoic acid. The 8S-DOX-AOS of Z. tritici transformed 18:2n-6 sequentially to 8S-HPODE and to an α-ketol, 8R-hydroxy-9-oxo-12Z-octadecenoic acid, likely formed by hydrolysis of 8S(9)-epoxy-9,12Z-octadecadienoic acid. The 8S-DOX-AOS oxidized [8R-2H]18:2n-6 to 8S-HPODE with retention of the 2H-label, suggesting suprafacial hydrogen abstraction and oxygenation in contrast to 8R-DOX-AOS. Both enzymes oxidized 18:1n-9 and 18:3n-3 to α-ketols, but the catalysis of the 8R- and 8S-AOS domains differed. 8R-DOX-AOS transformed 9R-HPODE to epoxy alcohols, but 8S-DOX-AOS converted 9S-HPODE to an α-ketol (9-hydroxy-10-oxo-12Z-octadecenoic acid) and epoxy alcohols in a ratio of ∼1:2. Whereas all fatty acid allene oxides described so far have a conjugated diene impinging on the epoxide, the allene oxides formed by 8-DOX-AOS are unconjugated. | - |
dc.format.extent | 11 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | American Society for Biochemistry and Molecular Biology | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.1194/jlr.M068981 | - |
dc.relation.ispartof | Journal of Lipid Research, 2016, vol. 57, num. 8, p. 1518-1528 | - |
dc.relation.uri | https://doi.org/10.1194/jlr.M068981 | - |
dc.rights | (c) American Society for Biochemistry and Molecular Biology, 2016 | - |
dc.source | Articles publicats en revistes (Ciències Fisiològiques) | - |
dc.subject.classification | Metabolisme dels lípids | - |
dc.subject.classification | Enzims | - |
dc.subject.classification | Dioxines | - |
dc.subject.classification | Proteïnes | - |
dc.subject.classification | Fongs patògens | - |
dc.subject.other | Lipid metabolism | - |
dc.subject.other | Enzymes | - |
dc.subject.other | Dioxins | - |
dc.subject.other | Proteins | - |
dc.subject.other | Pathogenic fungi | - |
dc.title | A new class of fatty acid allene oxide formed by the DOX-P450 fusion proteins of human and plant pathogenic fungi, C. immitis and Z. tritic | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 681429 | - |
dc.date.updated | 2018-10-09T11:53:41Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 27282156 | - |
Appears in Collections: | Articles publicats en revistes (Ciències Fisiològiques) |
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File | Description | Size | Format | |
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681429.pdf | 1.62 MB | Adobe PDF | View/Open |
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