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On the singular, dual, and multiple positional specificity of manganese lipoxygenase and its G316A mutant
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences. (Biochemical Pharmacology)
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences. (Biochemical Pharmacology)
2007 (English)In: Journal of Lipid Research, ISSN 0022-2275, E-ISSN 1539-7262, Vol. 48, no 4, 890-903 p.Article in journal (Refereed) Published
Abstract [en]

Manganese lipoxygenase (Mn-LO) oxygenates 18:3n-3 and 18:2n-6 to bis-allylic 11S-hydroperoxy fatty acids, which are converted to 13R-hydroperoxy fatty acids. Other unsaturated C16-C22 fatty acids, except 17:3n-3, are poor substrates, possibly due to ineffective enzyme activation (MnIIMnIII) by produced hydroperoxides. Our aim was to determine whether unsaturated C16-C22 fatty acids were oxidized by MnIII-LO. MnIII-LO oxidized C16, C19, C20, and C22 n-3 and n-6 fatty acids. The carbon chain length influenced the position of hydrogen abstraction (n-8, n-5) and oxygen insertion at the terminal or the penultimate 1Z,4Z-pentadienes. Dilinoleoyl¬glycero¬phosphatidyl¬¬choline was oxidized by Mn-LO in agreement with a “tail first” model. 16:3n-3 was oxidized at the bis-allylic n-5 carbon and at positions n-3, n-7, and n-6. Long fatty acids, 19:3n-3, 20:3n-3, 20:4n-6, 22:5n-3, and 22:5n-6, were mainly oxidized at the n-6 and the bis-allylic n-8 positions (in ratios of ~3:2). The bis-allylic hydroperoxides accumulated with one exception, 13-hydroperoxyeicosatetraenoic acid (13-HPETE). MnIII-LO oxidized 20:4n-6 to 15R-HPETE (~60%) and 13-HPETE (~37%) and converted 13-HPETE to 15R-HPETE. MnIII-LO G316A mainly oxygenated 16:3n-3 at positions n-7 and n-6, 19:3n-3 at n-10, n-8, and n-6, 20:3n-3 at n-10 and n-8. We conclude that Mn-LO likely binds fatty acids “tail first” and oxygenates many C16, C18, C20 and C22 fatty acids to significant amounts of bis-allylic hydroperoxides.

Place, publisher, year, edition, pages
2007. Vol. 48, no 4, 890-903 p.
Keyword [en]
nonconjugated peroxyls, fatty acid oxygenation, hydroperoxide isomerase, mass spectrometry, metalloenzymes, dilinoleoyl-glycerophosphatidylcholine, thermostability
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-23690DOI: 10.1194/jlr.M600505-JLR200ISI: 000245627100015PubMedID: 17259599OAI: oai:DiVA.org:uu-23690DiVA: diva2:51464
Available from: 2008-02-04 Created: 2008-02-04 Last updated: 2017-12-07Bibliographically approved

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Oliw, Ernst H.

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