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

Primdahl, Karoline Gangestad; Tungen, Jørn Eivind; De Souza, Patricia R; Colas, Romain A.; Dalli, Jesmond; Hansen, Trond Vidar; Vik, Anders
Journal article; AcceptedVersion; Peer reviewed
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Postprint+OBC+e ... -ART-08-2017-002113-R2.pdf (332.9Kb)
Year
2017
Permanent link
http://urn.nb.no/URN:NBN:no-66328

CRIStin
1502875

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  • Farmasøytisk institutt [1342]
  • CRIStin høstingsarkiv [15003]
Original version
Organic and biomolecular chemistry. 2017, 15 (40), 8606-8613, DOI: http://dx.doi.org/10.1039/c7ob02113e
Abstract
PD1n-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 PD1n-3 DPA from n-3 docosapentaenoic acid, the epoxy acid 16(S),17(S)-epoxy-PDn-3 DPA, herein named ePDn-3 DPA, was prepared by stereoselective total synthesis. The synthetic material of ePDn-3 DPA allowed investigations of its role in the biosynthesis of PD1n-3 DPA. The obtained results establish that the biosynthesis of PD1n-3 DPA in neutrophils occurs with ePDn-3 DPA as the intermediate, and that 15-LOX produces ePDn-3 DPA from n-3 docosapentaenoic acid. Furthermore, support for the involvement of a hydrolytic enzyme in the biosynthetic conversion of ePDn-3 DPA to PD1n-3 DPA was found. In addition, ePDn-3 DPA was found to regulate the formation of the potent neutrophil chemoattractant LTB4 with equal potencies to that obtained with PD1n-3 DPA.
 
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