ALOX5 oxidises 14(S)-Hp-DPAn-3 to MaR3n-3 DPA

Stable Identifier
Reaction [transition]
Homo sapiens
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In an alternative reaction to epoxidation, 14(S)-hydroperoxy-docosapentaenoic acid (14(S)-HpDPAn-3) can undergo a second oxygenation at the ω-1 position to yield 14(S), 21-dihydroxy-docosapentaenoic acid (MaR3n-3 DPA) (Dalli et al. 2013). MaR3n-3 DPA is named after maresin-1 (derived from DHA) as they share an alcohol group at C14 and is proposed to possess similar anti-inflammatory and proresolving potency and activity as maresin-1. With human leukocytes this n-3 DPA-SPM reduced neutrophil chemotaxis, adhesion and enhanced macrophage phagocytosis (Dalli et al. 2013, Vik et al. 2017). If, as assumed, DPA metabolism follows the same path as DHA metabolism, the lipoxygenase could be the dual-functional 5-lipoxygenase (ALOX5).

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

Serhan, CN, Colas, RA, Dalli, J

Sci Rep 2013
28408222 Recent advances in the chemistry and biology of anti-inflammatory and specialized pro-resolving mediators biosynthesized from n-3 docosapentaenoic acid

Hansen, TV, Vik, A, Dalli, J

Bioorg. Med. Chem. Lett. 2017
Catalyst Activity

arachidonate 5-lipoxygenase activity of ALOX5 [cytosol]

Orthologous Events
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