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The First Total Synthesis of the Lipid Mediator PD2 n-3 DPA

Authors
  • Tungen, Jørn Eivind1
  • Primdahl, Karoline Gangestad1
  • Hansen, Trond Vidar1
  • 1 University of Oslo, Norway , (Norway)
Type
Published Article
Journal
Journal of Natural Products
Publisher
American Chemical Society
Publication Date
Jun 16, 2020
Volume
83
Issue
7
Pages
2255–2260
Identifiers
DOI: 10.1021/acs.jnatprod.0c00385
PMID: 32543839
PMCID: PMC7467816
Source
PubMed Central
License
Unknown

Abstract

The resolution of inflammation is governed by the active biosynthesis of specialized pro-resolving mediators using ω-6 and ω-3 polyunsaturated fatty acids as substrates. These mediators act as resolution agonists and display several interesting bioactivities. PD2n-3 DPA is an oxygenated polyunsaturated fatty acid biosynthesized from n-3 docosapentaenoic acid belonging to the specialized pro-resolving lipid mediator family named protectins. The protectins exhibit anti-inflammatory properties and pro-resolving bioactivities. These endogenously produced compounds are of interest as leads in resolution pharmacology and drug development. Herein, together with its NMR, MS, and UV data, a stereoselective total synthesis of PD2n-3 DPA is presented.

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