EC 4.2.1.92 - Hydroperoxide dehydratase

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IntEnz Enzyme Nomenclature
EC 4.2.1.92

Names

Accepted name:
hydroperoxide dehydratase
Other names:
HPI
hydroperoxide isomerase
linoleate hydroperoxide isomerase
linoleic acid hydroperoxide isomerase
allene oxide synthase
(9Z,11E,14Z)-(13S)-hydroperoxyoctadeca-9,11,14-trienoate 12,13-hydro-lyase
(9Z,11E,14Z)-(13S)-hydroperoxyoctadeca-9,11,14-trienoate 12,13-hydro-lyase [(9Z)-(13S)-12,13-epoxyoctadeca-9,11-dienoate-forming]
AOS
Systematic name:
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate 12,13-hydro-lyase [(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate-forming]

Reaction

Cofactor

Comments:

Acts on a number of unsaturated fatty-acid hydroperoxides, forming the corresponding allene oxides. The product of the above reaction is unstable and is acted upon by EC 5.3.99.6, allene-oxide cyclase, to form the cyclopentenone derivative (15Z)-12-oxophyto-10,15-dienoate (OPDA), which is the first cyclic and biologically active metabolite in the jasmonate biosynthesis pathway [3]. The enzyme from many plants belongs to the CYP-74 family of P450 monooxygenases [4].

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Protein domains and families: PROSITE:PDOC00081
Structural data: CSA , EC2PDB
Gene Ontology: GO:0009978
UniProtKB/Swiss-Prot: (10) [show] [UniProt]

References

  1. Esselman, W.J. and Clagett, C.O.
    Products of linoleic hydroperoxide-decomposing enzyme of alfalfa seed.
    J. Lipid Res. 15 : 173-178 (1974). [PMID: 4208994]
  2. Hamberg, M.
    Mechanism of corn hydroperoxide isomerase - detection of 12,13(S)-oxido-9(Z),11-octadecadienoic acid.
    Biochim. Biophys. Acta 920 : 76-84 (1987).
  3. Hamberg, M.
    Biosynthesis of 12-oxo-10,15(Z)-phytodienoic acid: identification of an allene oxide cyclase.
    Biochem. Biophys. Res. Commun. 156 : 543-550 (1988). [PMID: 3178850]
  4. Laudert, D., Pfannschmidt, U., Lottspeich, F., Holländer-Czytko, H. and Weiler, E.W.
    Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP 74), the first enzyme of the octadecanoid pathway to jasmonates.
    Plant Mol. Biol. 31 : 323-335 (1996). [PMID: 8756596]

[EC 4.2.1.92 created 1992, modified 2008]