title: 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.
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.
authors.affiliation: Institut des Biomolécules Max Mousseron,UMR 5247 - CNRS - University Montpellier I and II - ENSCM, Faculty of Pharmacy, Montpellier (France), Fax: (+33) 411759553.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Guy
authors.forename: Camille
authors.initials: C
authors.lastname: Oger
authors.forename: Johannes
authors.initials: J
authors.lastname: Heppekausen
authors.forename: Cinzia
authors.initials: C
authors.lastname: Signorini
authors.forename: Claudio
authors.initials: C
authors.lastname: De Felice
authors.forename: Alois
authors.initials: A
authors.lastname: Fürstner
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Galano
mesh_terms: D015415:Biomarkers / Q000378:metabolism*; D015525:Fatty Acids, Omega-3 / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D015394:Molecular Structure; D018384:Oxidative Stress
chemical_list: D015415:Biomarkers; D015525:Fatty Acids, Omega-3; D005231:Fatty Acids, Unsaturated
keywords: NeuroPs; fatty acids; oxygenated metabolites; ring-closing metathesis; total synthesis