KEGG   ENZYME: 4.2.1.92
Entry
EC 4.2.1.92                 Enzyme                                 

Name
hydroperoxide dehydratase;
hydroperoxide isomerase;
linoleate hydroperoxide isomerase;
linoleic acid hydroperoxide isomerase;
HPI;
(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];
allene oxide synthase;
AOS
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
Sysname
(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(IUBMB)
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O [RN:R07863]
Reaction(KEGG)
R07863;
(other) R07865
Substrate
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate [CPD:C04785]
Product
(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate [CPD:C04672];
H2O [CPD:C00001]
Comment
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 P-450 monooxygenases [4].
History
EC 4.2.1.92 created 1992, modified 2008
Pathway
ec00592  alpha-Linolenic acid metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K01723  hydroperoxide dehydratase
Genes
ATH: AT5G42650(AOS)
ALY: 9299830 9301581
CRB: 17875394
CSAT: 104725217 104760703 104771391
EUS: EUTSA_v10003180mg
BRP: 103848557
BNA: 106367432 106429839 106446378 106446379
BOE: 106327419
RSZ: 108828933
THJ: 104803399 104806952 104819457
CIT: 102578025(AOS) 102614058
GMX: 100037481(AOS1) 100037482(AOS2) 100801764(CYP74A1) 100807192 100810890
LJA: Lj1g3v1604250.1(Lj1g3v1604250.1) Lj2g3v0000280.1(Lj2g3v0000280.1) Lj5g3v0080890.1(Lj5g3v0080890.1)
CSV: 101211324(HPL) 101211574 101221732(AOS)
CMO: 103487935(AOS) 103495194 103495195(HPL)
MCHA: 111008047
RCU: 8260919
SOT: 102577479(AOS) 102584249(aos3) 102588560 102589003(aos1)
DCR: 108223756
DOSA: Os02t0218700-01(Os02g0218700) Os02t0218800-01(Os02g0218800) Os03t0225900-01(Os03g0225900) Os03t0767000-01(Os03g0767000)
ATS: 109733275(LOC109733275) 109733277(LOC109733277) 109775278(LOC109775278) 109779482(LOC109779482)
ATR: 18446004
SMO: SELMODRAFT_133317(CYP74J1)
 » show all
Reference
1  [PMID:4208994]
  Authors
Esselman WJ, Clagett CO.
  Title
Products of linoleic hydroperoxide-decomposing enzyme of alfalfa seed.
  Journal
J Lipid Res 15:173-8 (1974)
Reference
2
  Authors
Hamberg, M.
  Title
Mechanism of corn hydroperoxide isomerase - detection of 12,13(S)-oxido-9(Z),11-octadecadienoic acid.
  Journal
Biochim Biophys Acta 920:76-84 (1987)
Reference
3  [PMID:3178850]
  Authors
Hamberg M.
  Title
Biosynthesis of 12-oxo-10,15(Z)-phytodienoic acid: identification of an allene oxide cyclase.
  Journal
Biochem Biophys Res Commun 156:543-50 (1988)
DOI:10.1016/S0006-291X(88)80876-3
Reference
4  [PMID:8756596]
  Authors
Laudert D, Pfannschmidt U, Lottspeich F, Hollander-Czytko H, Weiler EW
  Title
Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP 74), the first enzyme of the octadecanoid pathway to jasmonates.
  Journal
Plant Mol Biol 31:323-35 (1996)
DOI:10.1007/BF00021793
  Sequence
[ath:AT5G42650]
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.92
IUBMB Enzyme Nomenclature: 4.2.1.92
ExPASy - ENZYME nomenclature database: 4.2.1.92
BRENDA, the Enzyme Database: 4.2.1.92

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