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On the singular, du...
On the singular, dual, and multiple positional specificity of manganese lipoxygenase and its G316A mutant
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- Cristea, Mirela (författare)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap,Biochemical Pharmacology
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- Oliw, Ernst H. (författare)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap,Biochemical Pharmacology
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(creator_code:org_t)
- 2007
- 2007
- Engelska.
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Ingår i: Journal of Lipid Research. - 0022-2275 .- 1539-7262. ; 48:4, s. 890-903
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- 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.
Ämnesord
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Farmaceutiska vetenskaper (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)
Nyckelord
- nonconjugated peroxyls
- fatty acid oxygenation
- hydroperoxide isomerase
- mass spectrometry
- metalloenzymes
- dilinoleoyl-glycerophosphatidylcholine
- thermostability
- PHARMACY
- FARMACI
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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