ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3

Stable Identifier
Reaction [transition]
Homo sapiens
Locations in the PathwayBrowser
SVG |   | PPTX  | SBGN
Click the image above or here to open this reaction in the Pathway Browser
The layout of this reaction may differ from that in the pathway view due to the constraints in pathway layout

In neutrophils, an unknown lipoxygenase may mediate hydrogen abstraction from 17(S)-hydroperoxy-docosapentaenoic acid (17(S)-Hp-DPAn-3) to form 16(S),17(S)-epoxy-docosapentaenoic acid (16(S),17(S)-epoxy-DPAn-3) (Dalli et al. 2013). If, as assumed, DPA metabolism follows the same path as DHA metabolism, the lipoxygenase could be the dual-functional 5-lipoxygenase (ALOX5). The formation of this epoxy intermediate is supported by chemical synthesis experiments (Aursnes et al. 2014, Primdahl et al. 2017).

Literature References
PubMed ID Title Journal Year
23736886 Novel n-3 immunoresolvents: structures and actions

Serhan, CN, Colas, RA, Dalli, J

Sci Rep 2013
24576195 Total synthesis of the lipid mediator PD1n-3 DPA: configurational assignments and anti-inflammatory and pro-resolving actions

Serhan, CN, Colas, RA, Cheng, CY, Hansen, TV, Tungen, JE, Aursnes, M, Vik, A, Dalli, J

J. Nat. Prod. 2014
28980694 Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA

Colas, RA, Hansen, TV, Tungen, JE, Vik, A, Dalli, J, Primdahl, KG, De Souza, PRS

Org. Biomol. Chem. 2017
Catalyst Activity

arachidonate 5-lipoxygenase activity of ALOX5 [cytosol]

Orthologous Events
Cite Us!