Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine |
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Authors: | Petrova Katya V Stec Donald F Voehler Markus Rizzo Carmelo J |
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Affiliation: | Department of Chemistry, Center in Molecular Toxicology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee, 37235-1822, USA. |
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Abstract: | 2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2'-deoxyguanosine. In addition to 1,N(2)-etheno-2'-deoxyguanosine, 12 stereoisomeric products were isolated and characterized by (1)H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture. |
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