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
cytosol
ReviewStatus
5/5
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ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3
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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
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
Participants
Input
Output
Participates
as an event of
Catalyst Activity

arachidonate 5-lipoxygenase activity of ALOX5 [cytosol]

Physical Entity
ALOX5 [cytosol] (Homo sapiens)
Activity
arachidonate 5-lipoxygenase activity (GO:0004051)
Orthologous Events
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Bos taurus)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Canis familiaris)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Danio rerio)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Dictyostelium discoideum)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Gallus gallus)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Mus musculus)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Rattus norvegicus)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Sus scrofa)
ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-3 (Xenopus tropicalis)
Authored
Jassal, B  (2017-10-16)
Reviewed
Hansen, TV  (2018-02-21)
Created
Jassal, B  (2017-10-16)
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