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Stereoselective oxi...
Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases
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- Oliw, Ernst H. (author)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap
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- Wennman, Anneli (author)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap
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- Hoffmann, Inga (author)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap
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- Garscha, Ulrike (author)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap
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- Hamberg, Mats (author)
- Karolinska Institutet
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- Jernerén, Fredrik (author)
- Uppsala universitet,Institutionen för farmaceutisk biovetenskap
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(creator_code:org_t)
- 2011
- 2011
- English.
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In: Journal of Lipid Research. - 0022-2275 .- 1539-7262. ; 52:11, s. 1995-2004
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https://doi.org/10.1...
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Abstract
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- Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C(14)-C(20) fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.
Keyword
- chiral phase HPLC
- cyclooxygenase
- enzymology/enzyme mechanisms
- fatty acid/oxygenation
- linoleate diol synthase
- manganese lipoxygenase
- mass spectrometry
Publication and Content Type
- ref (subject category)
- art (subject category)
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