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Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals.

Komaszylo, Joanna and Kania, Magdalena and Masnyk, Marek and Cmoch, Piotr and Lozinska, Iwona and Czarnocki, Zbigniew and Skorupinska-Tudek, Karolina and Danikiewicz, Witold and Swiezewska, Ewa (2016) Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals. Lipids, 51 (2). pp. 229-244. ISSN 0024-4201

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Isoprenoids, as common constituents of all living cells, are exposed to oxidative agents—reactive oxygen species, for example, singlet oxygen or hydroxyl radicals. Despite this fact, products of oxidation of polyisoprenoids have never been characterized. In this study, chemical oxidation of isoprenoid alcohols (Prenol-2 and -10) was performed using singlet oxygen (generated in the presence of hydrogen peroxide/molybdate or upon photochemical reaction in the presence of porphyrin), oxygen (formed upon hydrogen peroxide dismutation) or hydroxyl radical (generated by the hydrogen peroxide/sonication, UV/titanium dioxide or UV/hydrogen peroxide) systems. The structure of the obtained products, hydroxy-, peroxy- and heterocyclic derivatives, was studied with the aid of mass spectrometry (MS) and nuclear magnetic resonance (NMR) methods. Furthermore, mass spectrometry with electrospray ionization appeared to be a useful analytical tool to detect the products of oxidation of isoprenoids (ESI–MS analysis), as well as to establish their structure on the basis of the fragmentation spectra of selected ions (ESI–MS/MS analysis). Taken together, susceptibility of polyisoprenoid alcohols to various oxidizing agents was shown for the first time.

Item Type:Article
Subjects:Q Science > QH Natural history > QH301 Biology
Divisions:Department of Lipid Biochemistry
ID Code:1171
Deposited By: Ewa Swiezewska
Deposited On:19 Apr 2016 08:26
Last Modified:19 Apr 2016 08:26

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