Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)

Stable Identifier
R-HSA-2142816
Type
Pathway
Species
Homo sapiens
ReviewStatus
5/5
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Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)
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Similar to the lipoxygenases, cytochrome P450 (CYP) enzymes catalyse the hydroxylation and epoxygenation of arachidonate. However, whereas lipoxygenases use an active non-heme iron to abstract hydrogen directly from arachidonate, CYPs contain a heme-iron active site that oxidizes its substrate by a different mechanism. They hydroxylate arachidonate between C-5 and C-15 to produce lipoxygenase-like hydroxyeicosatetraenoates (HETEs) and add a hydroxyl moiety to the sp3-hybridized omega-carbons to form a unique class of HETEs. The transfer of oxygen to the unstable arachidonate intermediate terminates the reaction by forming HETE or epoxy-eicosatrienoate (EETs), respectively (Capdevila et al. 2000, Buczynski et al. 2009, Vance & Vance 2008).
Literature References
PubMed ID Title Journal Year
10681399 Cytochrome P450 and arachidonic acid bioactivation. Molecular and functional properties of the arachidonate monooxygenase

Capdevila, JH, Falck, JR, Harris, RC

J Lipid Res 2000
  Biochemistry of Lipids, Lipoproteins and Membranes, 5th Edition

Vance, DE, Vance, JE

  2008
19244215 Thematic Review Series: Proteomics. An integrated omics analysis of eicosanoid biology

Buczynski, MW, Dumlao, DS, Dennis, EA

J Lipid Res 2009
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Event Information
Go Biological Process
omega-hydroxylase P450 pathway (0097267)
Orthologous Events
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Bos taurus)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Caenorhabditis elegans)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Canis familiaris)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Danio rerio)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Dictyostelium discoideum)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Drosophila melanogaster)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Gallus gallus)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Mus musculus)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Rattus norvegicus)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Sus scrofa)
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (Xenopus tropicalis)
Authored
Williams, MG  (2012-02-24)
Reviewed
Rush, MG  (2012-11-10)
Hill, DP  (2024-08-02)
Created
Williams, MG  (2012-02-24)
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