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Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2_{n-3 DPA}.

ABSTRACT: Herein we report the first total synthesis of RvD2_{n-3 DPA} , 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_{n-3 DPA} 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_{n-3 DPA} also carried the potent biological activities of enhancing macrophage uptake of Staphylococcus aureus and zymosan A bioparticles.

SUBMITTER: Reinertsen AF

PROVIDER: S-EPMC9305452 | biostudies-literature |

REPOSITORIES: biostudies-literature

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