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Kinetic studies of retinol addition radicals

Title
Kinetic studies of retinol addition radicals
Authors
El-Agamey A.Fukuzumi S.Naqvi K.R.McGarvey D.J.
Ewha Authors
Shunichi Fukuzumi
SCOPUS Author ID
Shunichi Fukuzumiscopus
Issue Date
2011
Journal Title
Organic and Biomolecular Chemistry
ISSN
1477-0520JCR Link
Citation
vol. 9, no. 5, pp. 1459 - 1465
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Retinol neutral radicals (RS-retinol), generated from the reaction of retinol with 4-pyridylthiyl and 2-pyridylthiyl radicals in argon-saturated methanol, undergo β-elimination, which can be monitored via the slow secondary absorption rise at 380 nm attributed to the rearrangement of the unstable retinol neutral addition radicals to the more stable addition radicals. Rate constants for the β-elimination reactions (kβ) of 4-PyrS-retinol were measured at different temperatures and the Arrhenius equation for the reaction is described by log (kβ/s -1) = (12.7 ± 0.2) - (54.3 ± 1.3)/, where = 2.3RT kJ mol-1. The reactivities of retinol addition radicals (RS-retinol), generated from the reaction of retinol with various thiyl radicals, towards oxygen have also been investigated in methanol. In the presence of oxygen, the decay of RS-retinol fits to biexponential kinetics and both observed rate constants for the RS-retinol decay are oxygen-concentration dependent. This suggests that at least two thiyl addition radicals, formed from the reaction of RS with retinol, undergo oxygen addition reactions. In light of the estimated rate constants for oxygen addition to RS-retinol and RS-CAR (CAR: carotenoid), the antioxidant-prooxidant properties of retinol are discussed. © The Royal Society of Chemistry 2011.
DOI
10.1039/c0ob00799d
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자연과학대학 > 화학·나노과학전공 > Journal papers
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