Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2 n-3 DPA

Herein we report the first total synthesis of RvD2 , an endogenously formed mediator biosynthesized from the omega-3 fatty acid n-3 docosapentaenoic acid. The key steps are the Midland Alpine borane reduction, Sonogashira cross-coupling reactions, and a Z-selective alkyne reduction protocol, yieldin...

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Bibliographic Details
Published in:Chemistry : a European journal 2022-02, Vol.28 (7), p.e202103857
Main Authors: Reinertsen, Amalie F, Primdahl, Karoline G, De Matteis, Roberta, Dalli, Jesmond, Hansen, Trond V
Format: Article
Language:English
Subjects:
Docosahexaenoic Acids
Fatty Acids, Omega-3
Macrophages
Tandem Mass Spectrometry
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Summary:Herein we report the first total synthesis of RvD2 , an endogenously formed mediator biosynthesized from the omega-3 fatty acid n-3 docosapentaenoic acid. The key steps are the Midland Alpine borane reduction, Sonogashira cross-coupling reactions, and a Z-selective alkyne reduction protocol, yielding RvD2 methyl ester in 13 % yield over 12 steps (longest linear sequence). The physical property data (UV chromophore, chromatography and MS/MS fragmentation) of the synthetic lipid mediator matched those obtained from biologically produced material. Moreover, synthetic RvD2 also carried the potent biological activities of enhancing macrophage uptake of Staphylococcus aureus and zymosan A bioparticles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202103857