A wide variety of metabolic products of polyunsaturated fatty acids is of paramount importance for improving our medical knowledge in the field of oxidized lipids. Two novel metabolites of n-3 polyunsaturated fatty acids, 8-F3t-IsoP and 10-F4t-NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8-F3t-IsoP by a ring-closing alkyne metathesis/semi-reduction strategy together with a temporary tether. Three for the price of one! Two strategies, Caruso coupling or ring-closing alkyne metathesis (RCAM), enabled the synthesis of 8-F 3t-IsoP and 10-F4t-NeuroP and its deuterated derivative from acetylenic intermediateA (see scheme). Such compounds represent potential biomarkers of neuronal oxidative stress. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Guy, A., Oger, C., Heppekausen, J., Signorini, C., De Felice, C., Fürstner, A., et al. (2014). Oxygenated metabolites of n-3 polyunsaturated fatty acids as potential oxidative stress biomarkers: total synthesis of 8-F3t-IsoP, 10-F4t-NeuroP and [D4]-10-F4t-NeuroP. CHEMISTRY-A EUROPEAN JOURNAL, 20(21), 6374-6380 [10.1002/chem.201400380].
Oxygenated metabolites of n-3 polyunsaturated fatty acids as potential oxidative stress biomarkers: total synthesis of 8-F3t-IsoP, 10-F4t-NeuroP and [D4]-10-F4t-NeuroP
Signorini, C.;
2014-01-01
Abstract
A wide variety of metabolic products of polyunsaturated fatty acids is of paramount importance for improving our medical knowledge in the field of oxidized lipids. Two novel metabolites of n-3 polyunsaturated fatty acids, 8-F3t-IsoP and 10-F4t-NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8-F3t-IsoP by a ring-closing alkyne metathesis/semi-reduction strategy together with a temporary tether. Three for the price of one! Two strategies, Caruso coupling or ring-closing alkyne metathesis (RCAM), enabled the synthesis of 8-F 3t-IsoP and 10-F4t-NeuroP and its deuterated derivative from acetylenic intermediateA (see scheme). Such compounds represent potential biomarkers of neuronal oxidative stress. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.File | Dimensione | Formato | |
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https://hdl.handle.net/11365/47873
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