Total Synthesis of DHA and DPA_n-3 Non-Enzymatic Oxylipins

Abstract

Oxylipins are formed in vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentane, tetrahydrofuran, hydroxylated-PUFA, etc.). All structures of oxylipins are of great biological interest. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies, and more especially, they were found to have their own biological properties. Produced in vivo as a non-separable mixture of isomers, their total synthesis is a keystone to answer biological questions. In this work, the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPA_n-3) is described using a unique and convergent synthetic strategy.

Key words

total synthesis - oxidative stress - biomarkers - neuroprostanes - non-enzymatic oxylipins

Publication History

Received: 21 July 2021

Accepted after revision: 27 September 2021

Accepted Manuscript online:
27 September 2021

Article published online:
17 November 2021

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