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

Stable Identifier
R-HSA-9025999
Type
Reaction [transition]
Species
Homo sapiens
Compartment
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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
24576195 Total synthesis of the lipid mediator PD1n-3 DPA: configurational assignments and anti-inflammatory and pro-resolving actions

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

J. Nat. Prod. 2014
23736886 Novel n-3 immunoresolvents: structures and actions

Dalli, J, Colas, RA, Serhan, CN

Sci Rep 2013
28980694 Stereocontrolled synthesis and investigation of the biosynthetic transformations of 16(S),17(S)-epoxy-PDn-3 DPA

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

Org. Biomol. Chem. 2017
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Participates
Catalyst Activity

arachidonate 5-lipoxygenase activity of ALOX5 [cytosol]

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