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Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA
Author(s) -
Oger Camille,
BultelPoncé Valérie,
Guy Alexandre,
Durand Thierry,
Galano JeanMarie
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200070
Subject(s) - isoprostanes , chemistry , polyunsaturated fatty acid , eicosapentaenoic acid , myelin , biochemistry , fatty acid , arachidonic acid , enzyme , central nervous system , biology , neuroscience
Enantiomerically enriched F 2 ‐dihomo‐isoprostanes and F 3 ‐isoprostanes have been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid‐bound polyunsaturated fatty acids (PUFA), adrenic acid and eicosapentaenoic acid, respectively. Of special interest are the F 2 ‐dihomo‐isoprostanes because they could represent potential biomarkers for myelin damage as its main PUFA constituent is adrenic acid. Our strategy, based on a pivotal enantiomerically enriched intermediate, has allowed access to F 2 ‐dihomo‐IsoP and both C5 epimers of 5‐F 3t ‐IsoP for the first time.