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PD1 n-3 DPA is a specialized pro-resolving lipid mediator that displays potent anti-inflammatory properties and pro-resolving bioactivities. Such naturally occurring compounds are of current interest in biomolecular chemistry and drug discovery. To investigate the involvement of an epoxide intermediate in the biosynthesis of PD1 n-3 DPA from n-3 docosapentaenoic acid, the epoxy acid 16(S),17(S)-epoxy-PD n-3 DPA , herein named ePD n-3 DPA , was prepared by stereoselective total synthesis. The synthetic material of ePD n-3 DPA allowed investigations of its role in the biosynthesis of PD1 n-3 DPA . The obtained results establish that the biosynthesis of PD1 n-3 DPA in neutrophils occurs with ePD n-3 DPA as the intermediate, and that 15-LOX produces ePD n-3 DPA from n-3 docosapentaenoic acid. Furthermore, support for the involvement of a hydrolytic enzyme in the biosynthetic conversion of ePD n-3 DPA o PD1 n-3 DPA was found. In addition, ePD n-3 DPA was found to regulate the formation of the potent neutrophil chemoattractant LTB 4 with equal potencies to that obtained with PD1 n-3 DPA .

Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA

Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PD_{n-3 DPA}