The First Total Synthesis of the Lipid Mediator PD2n-3 DPA

J Nat Prod. 2020 Jul 24;83(7):2255-2260. doi: 10.1021/acs.jnatprod.0c00385. Epub 2020 Jun 16.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Humans
  • Molecular Structure
  • Spectrum Analysis / methods
  • Substrate Specificity

Substances

  • Fatty Acids, Unsaturated