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

被引：69

作者：

Guy, Alexandre ^{[1
]}

Oger, Camille ^{[1
]}

Heppekausen, Johannes ^{[2
]}

Signorini, Cinzia ^{[3
]}

De Felice, Claudio ^{[4
]}

Fuerstner, Alois ^{[2
]}

Durand, Thierry ^{[1
]}

Galano, Jean-Marie ^{[1
]}

机构：

[1] Univ Montpellier I & II, Inst Biomol Max Mousseron, CNRS, UMR 5247,ENSCM,Fac Pharm, Montpellier, France

[2] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

[3] Univ Siena, Dept Mol & Dev Med, I-53100 Siena, Italy

[4] AOUS, Univ Hosp, Neonatal Intens Care Unit, Siena, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 21期

关键词：

fatty acids; NeuroPs; oxygenated metabolites; ring-closing metathesis; total synthesis; CLOSING ALKYNE METATHESIS; PROTECTING-GROUP-FREE; 1ST TOTAL SYNTHESIS; SECONDARY ALCOHOLS; RETT-SYNDROME; METHYL-ESTER; ISOPROSTANES; NEUROPROSTANES; F-4-NEUROPROSTANES; ECKLONIALACTONES;

D O I：

10.1002/chem.201400380

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-F-3t-IsoP and 10-F-4t-NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8-F-3t-IsoP by a ring-closing alkyne metathesis/semi-reduction strategy together with a temporary tether.

引用

页码：6374 / 6380

页数：7

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