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

Jørn E. Tungen | Zendy; Karoline Gangestad Primdahl | Zendy; Trond Vidar Hansen | Zendy

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The First Total Synthesis of the Lipid Mediator PD2_{n-3 DPA}

Author(s) -

Jørn E. Tungen,

Karoline Gangestad Primdahl,

Trond Vidar Hansen

Publication year - 2020

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.0c00385

Subject(s) - docosapentaenoic acid , polyunsaturated fatty acid , lipid signaling , chemistry , mediator , resolution (logic) , stereoselectivity , biosynthesis , stereochemistry , total synthesis , biochemistry , fatty acid , chemical synthesis , high resolution , biology , eicosapentaenoic acid , in vitro , enzyme , microbiology and biotechnology , artificial intelligence , computer science , catalysis , remote sensing , geology

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. PD2 n-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 PD2 n-3 DPA is presented.

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