Synthesis and spin-trapping behavior of 5-ChEPMPO, a cholesteryl ester analogue of the spin trap DEPMPO

Micaël Hardy, Olivier Ouari, Laurence Charles, Jean Pierre Finet, Gilles Iacazio, Valérie Monnier, Antal Rockenbauer, Paul Tordo

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

5-(Cholesteryloxyethoxyphosphoryl)-5-methylpyrroline N-oxide (5-ChEPMPO), a DEPMPO analogue bearing a cholesterol group on the phosphorus atom, has been prepared and used to trap peroxyl-, alkoxyl-, thiyl-, and carbon-centered radicals in organic solvent. The important steric hindrance in 5-ChEPMPO does not affect the properties of 5-ChEPMPO in comparison to DEPMPO for the spin trapping of an enantiopure linoleic acid hydroperoxide. The 5-ChEPMPO-OOL spin adduct was observed by ESR and confirmed by ESI-MS/MS experiments. The relaxation terms of the 5-ChEPMPO-lipid peroxyl spin adduct were compared with those of other peroxyl spin adducts, and it was shown that the cholesteryl group has only a weak influence on the exchange rate between adduct conformers.

Original languageEnglish
Pages (from-to)10426-10433
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number25
DOIs
Publication statusPublished - Dec 9 2005

ASJC Scopus subject areas

  • Organic Chemistry

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