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Theoretical modeling of hydroxyl-radical-induced lipid peroxidation reactions
Örebro University, Department of Natural Sciences. (Biophysical Chemistry)
2007 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 111, no 20, p. 5684-5693Article in journal (Refereed) Published
Abstract [en]

The OH-radical-induced mechanism of lipid peroxidation, involving hydrogen abstraction followed by O2 addition, is explored using the kinetically corrected hybrid density functional MPWB1K in conjunction with the MG3S basis set and a polarized continuum model to mimic the membrane interior. Using a small nonadiene model of linoleic acid, it is found that hydrogen abstraction preferentially occurs at the mono-allylic methylene groups at the ends of the conjugated segment rather than at the central bis-allylic carbon, in disagreement with experimental data. Using a full linoleic acid, however, abstraction is correctly predicted to occur at the central carbon, giving a pentadienyl radical. The Gibbs free energy for abstraction at the central C11 is 8 kcal/mol, compared to 9 kcal/mol at the end points (giving an allyl radical). Subsequent oxygen addition will occur at one of the terminal atoms of the pentadienyl radical fragment, giving a localized peroxy radical and a conjugated butadiene fragment, but is associated with rather high free energy barriers and low exergonicity at the CPCM-MPWB1K/MG3S level. The ZPE-corrected potential energy surfaces obtained without solvent effects, on the other hand, display considerably lower barriers and more exergonic reactions.

Place, publisher, year, edition, pages
American Chemical Society , 2007. Vol. 111, no 20, p. 5684-5693
Keywords [en]
Hydroxyl Radical, Lipid Peroxidation, Lipid Models, Molecular Structure, Thermodynamics, Computational Chemistry
National Category
Theoretical Chemistry Natural Sciences Chemical Sciences
Research subject
Physical Chemistry; Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-4106DOI: 10.1021/jp0650782PubMedID: 17472362OAI: oai:DiVA.org:oru-4106DiVA, id: diva2:138405
Available from: 2007-11-02 Created: 2007-11-02 Last updated: 2017-12-14Bibliographically approved

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Eriksson, Leif A.

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