KEGG   ORTHOLOGY: K10529
Entry
K10529                      KO                                     
Symbol
DOX
Name
fatty acid alpha-dioxygenase [EC:1.13.11.92]
Pathway
map00592  alpha-Linolenic acid metabolism
map01110  Biosynthesis of secondary metabolites
Reaction
R12775  
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00592 alpha-Linolenic acid metabolism
    K10529  DOX; fatty acid alpha-dioxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.13  Acting on single donors with incorporation of molecular oxygen (oxygenases)
   1.13.11  With incorporation of two atoms of oxygen
    1.13.11.92  fatty acid alpha-dioxygenase
     K10529  DOX; fatty acid alpha-dioxygenase
Genes
ATH: AT1G73680(ALPHA_DOX2) AT3G01420(DOX1)
ALY: 9318251 9323562
CRB: 17875522 17892716 17895917
CSAT: 104712985 104722852 104725352 104744212 104751224 104760846 104763857 104767297
EUS: EUTSA_v10018266mg EUTSA_v10020279mg
BRP: 103830737 103831843 103852857 103870978
BNA: 106354295 106381357 106399154 106406119 106406278 106430143 106434296 106453030
BOE: 106295349 106296274 106301074 106344107
RSZ: 108818535 108827277 108832490 108861282
THJ: 104822381 104823467
CPAP: 110823287
CIT: 102610137 102610448 102611343
CIC: CICLE_v10007736mg CICLE_v10014579mg CICLE_v10014631mg
PVY: 116111901 116117480 116143562
MINC: 123204521 123222456 123222876 123224525 123224526 123224529
TCC: 18600713
GRA: 105780850 105780851 105800062
GHI: 107899049 107900136 107925999 107938825 107959828 121216311 121226453
GAB: 108454599 108458092 108458899
HSYR: 120138537 120138538 120176149 120187913
DZI: 111315948
EGR: 104425827
GMX: 100794600 100797235 100817200
GSJ: 114381454 114400167 114400168
PVU: PHAVU_004G018900g PHAVU_004G019000g
VRA: 106770738 106770747 106775070
VAR: 108345851
VUN: 114180384 114180911 114181682 114182677
VUM: 124840424
CCAJ: 109799552 109812578 109817957
APRC: 113853890 113867410
MTR: 11412210 25495214 25495215 25495216
TPRA: 123906525 123906526 123906527 123913513
CAM: 101490863(piox) 101504934 101509878
PSAT: 127105052 127119991 127119996 127120013 127120023 127120033
VVO: 131603978 131647270 131647275 131650469 131652761 131652762 131652763 131652770
LJA: 130715462 130739257
ADU: 107490814 107490985
AIP: 107643991
AHF: 112750754 112750755 112802506
LANG: 109330607 109336245 109347296
PCIN: 129306273 129319529
QSA: O6P43_004582 O6P43_008371 O6P43_008504
PPER: 18777310
PMUM: 103338722
PAVI: 110746731
PDUL: 117628082
MDM: 103424608
MSYL: 126598680
PXB: 103950592
ZJU: 107418715 132799059
MNT: 21400402 21402311
CSAV: 115711497
CSV: 101206631 101218397 101218599 101218631
CMO: 103487064 103487066 103487178 103494169
BHJ: 120071394 120089994 120091882
MCHA: 111007075 111018335 111018381 111024652
CMAX: 111481867 111484802
CMOS: 111430137 111441943
CPEP: 111779807 111790326
RCU: 8260089 8280559 8280584
MEAN: 126665217 126671823 130014649 130015243
JCU: 105631044 105641982
HBR: 110632577 110651018 110651179 110651180
MESC: 110601345 110604715 110630830
POP: 112323590 7485908
PEU: 105122604 105135771
PALZ: 118046291 118062473
PNZ: 133677811 133704350
JRE: 108997156 108997157 108997763 109021239
CILL: 122296327 122299163 122306874 122308147
CAVE: 132182474 132182475 132182476 132182819 132182925 132184182
QSU: 111986908 111989242 112027093 112027097
QLO: 115956813 115963520 115978290 115978291
TWL: 119986662 120016501
VVI: 100254380 100260995
VRI: 117903985 117929448
SLY: 101246396 543806(alpha-DOX2) 543895 543896
SPEN: 107008707 107009547 107014721
SOT: 102578713 102579471 102583448 102583777 102584442
SSTN: 125846390 125846391 125846395 125847496 125858207
SDUL: 129874505 129874769 129874770 129874772 129894155 129895383
CANN: 107860613 107860616 107860618 107860619 107862200 107862202 124896124
LBB: 132624801 132625028 132633237 132641540
NTA: 107788054 107788258 107791409(oxygenase) 107792582 107806116 107811991 107813858
NSY: 104225473 104240825 104241681 104242207
NTO: 104093716 104095551 104096874
NAU: 109208731 109209670 109214392 109222069
INI: 109151261
ITR: 116018951 116020026
OEU: 111397003 111401399
SSPL: 121769123
SHIS: 125205603 125208429
APAN: 127257822 127258364
HAN: 110896133 110896135 110904031 110904034 110904035 110930525
ECAD: 122580503 122603312 122603728 122604752 122605464 122605846
LSV: 111876447 111876451 111915138
CCAV: 112511566 112512108 112512116 112512670 112524614 112525570
CSIN: 114318634 114318645 114318657
RVL: 131303768
AEW: 130768412
MOF: 131168094 131168196
NNU: 104587776 104595421 104595431
MING: 122081730 122081742 122094355
TSS: 122638333 122638340
PSOM: 113275454 113277622 113319234
OSA: 4352160
OGL: 127757523
ATS: 109758011
TDC: 119326475
TAES: 101290585 123072527 123072528
TUA: 125552198
ZMA: 101027254
PVIR: 120643818 120685624
PHAI: 112903103
PDA: 103698676 103714427
EGU: 105056278 105056286
MUS: 103973892 103998463
ZOF: 122050328 122051689 122056220
MSIN: 131218050 131218908 131218912 131218913 131235421
NCOL: 116249773
ATR: 18427569 18428104
SMO: SELMODRAFT_229898
PPP: 112278006
AG: CAH05011(alphaDOX1)
 » show all
Reference
PMID:10455113
  Authors
Hamberg M, Sanz A, Castresana C
  Title
alpha-oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (piox) as an alpha-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid.
  Journal
J Biol Chem 274:24503-13 (1999)
DOI:10.1074/jbc.274.35.24503
  Sequence
[ath:AT3G01420]
Reference
PMID:19759339
  Authors
Bannenberg G, Martinez M, Rodriguez MJ, Lopez MA, Ponce de Leon I, Hamberg M, Castresana C
  Title
Functional analysis of alpha-DOX2, an active alpha-dioxygenase critical for normal development in tomato plants.
  Journal
Plant Physiol 151:1421-32 (2009)
DOI:10.1104/pp.109.145094
  Sequence
[ath:AT1G73680]
Reference
PMID:18760499
  Authors
Meisner AK, Saffert A, Schreier P, Schon A.
  Title
Fatty acid alpha-dioxygenase from Pisum sativum: temporal and spatial regulation during germination and plant development.
  Journal
J Plant Physiol 166:333-43 (2009)
DOI:10.1016/j.jplph.2008.05.009
  Sequence
[ag:CAH05011]
LinkDB

KEGG   ENZYME: 1.13.11.92
Entry
EC 1.13.11.92               Enzyme                                 
Name
fatty acid alpha-dioxygenase;
DOX1 (gene name)
Class
Oxidoreductases;
Acting on single donors with incorporation of molecular oxygen (oxygenases);
With incorporation of two atoms of oxygen
Sysname
fatty acid:oxygen 2-oxidoreductase [(2R)-2-hydroperoxyfatty acid-forming]
Reaction(IUBMB)
a fatty acid + O2 = a (2R)-2-hydroperoxyfatty acid [RN:R12771]
Reaction(KEGG)
R12771 > R12775
Substrate
fatty acid [CPD:C00162];
O2 [CPD:C00007]
Product
(2R)-2-hydroperoxyfatty acid [CPD:C22387]
Comment
Contains heme. This plant enzyme catalyses the (2R)-hydroperoxidation of fatty acids. It differs from lipoxygenases and cyclooxygenases in that the oxygen addition does not target an unsaturated region in the fatty acid. In vitro the product undergoes spontaneous decarboxylation, resulting in formation of a chain-shortened aldehyde. In vivo the product may be reduced to a (2R)-2-hydroxyfatty acid. The enzyme, which is involved in responses to different abiotic and biotic stresses, has a wide substrate range that includes both saturated and unsaturated fatty acids.
History
EC 1.13.11.92 created 2021
Pathway
ec00592  alpha-Linolenic acid metabolism
ec01110  Biosynthesis of secondary metabolites
Orthology
K10529  fatty acid alpha-dioxygenase
Genes
ATH: AT1G73680(ALPHA_DOX2) AT3G01420(DOX1)
ALY: 9318251 9323562
CRB: 17875522 17892716 17895917
CSAT: 104712985 104722852 104725352 104744212 104751224 104760846 104763857 104767297
EUS: EUTSA_v10018266mg EUTSA_v10020279mg
BRP: 103830737 103831843 103852857 103870978
BNA: 106354295 106381357 106399154 106406119 106406278 106430143 106434296 106453030
BOE: 106295349 106296274 106301074 106344107
RSZ: 108818535 108827277 108832490 108861282
THJ: 104822381 104823467
CPAP: 110823287
CIT: 102610137 102610448 102611343
CIC: CICLE_v10007736mg CICLE_v10014579mg CICLE_v10014631mg
PVY: 116111901 116117480 116143562
MINC: 123204521 123222456 123222876 123224525 123224526 123224529
TCC: 18600713
GRA: 105780850 105780851 105800062
GHI: 107899049 107900136 107925999 107938825 107959828 121216311 121226453
GAB: 108454599 108458092 108458899
HSYR: 120138537 120138538 120176149 120187913
DZI: 111315948
EGR: 104425827
GMX: 100794600 100797235 100817200
GSJ: 114381454 114400167 114400168
PVU: PHAVU_004G018900g PHAVU_004G019000g
VRA: 106770738 106770747 106775070
VAR: 108345851
VUN: 114180384 114180911 114181682 114182677
VUM: 124840424
CCAJ: 109799552 109812578 109817957
APRC: 113853890 113867410
MTR: 11412210 25495214 25495215 25495216
TPRA: 123906525 123906526 123906527 123913513
CAM: 101490863(piox) 101504934 101509878
PSAT: 127105052 127119991 127119996 127120013 127120023 127120033
VVO: 131603978 131647270 131647275 131650469 131652761 131652762 131652763 131652770
LJA: 130715462 130739257
ADU: 107490814 107490985
AIP: 107643991
AHF: 112750754 112750755 112802506
LANG: 109330607 109336245 109347296
PCIN: 129306273 129319529
QSA: O6P43_004582 O6P43_008371 O6P43_008504
PPER: 18777310
PMUM: 103338722
PAVI: 110746731
PDUL: 117628082
MDM: 103424608
MSYL: 126598680
PXB: 103950592
ZJU: 107418715 132799059
MNT: 21400402 21402311
CSAV: 115711497
CSV: 101206631 101218397 101218599 101218631
CMO: 103487064 103487066 103487178 103494169
BHJ: 120071394 120089994 120091882
MCHA: 111007075 111018335 111018381 111024652
CMAX: 111481867 111484802
CMOS: 111430137 111441943
CPEP: 111779807 111790326
RCU: 8260089 8280559 8280584
MEAN: 126665217 126671823 130014649 130015243
JCU: 105631044 105641982
HBR: 110632577 110651018 110651179 110651180
MESC: 110601345 110604715 110630830
POP: 112323590 7485908
PEU: 105122604 105135771
PALZ: 118046291 118062473
PNZ: 133677811 133704350
JRE: 108997156 108997157 108997763 109021239
CILL: 122296327 122299163 122306874 122308147
CAVE: 132182474 132182475 132182476 132182819 132182925 132184182
QSU: 111986908 111989242 112027093 112027097
QLO: 115956813 115963520 115978290 115978291
TWL: 119986662 120016501
VVI: 100254380 100260995
VRI: 117903985 117929448
SLY: 101246396 543806(alpha-DOX2) 543895 543896
SPEN: 107008707 107009547 107014721
SOT: 102578713 102579471 102583448 102583777 102584442
SSTN: 125846390 125846391 125846395 125847496 125858207
SDUL: 129874505 129874769 129874770 129874772 129894155 129895383
CANN: 107860613 107860616 107860618 107860619 107862200 107862202 124896124
LBB: 132624801 132625028 132633237 132641540
NTA: 107788054 107788258 107791409(oxygenase) 107792582 107806116 107811991 107813858
NSY: 104225473 104240825 104241681 104242207
NTO: 104093716 104095551 104096874
NAU: 109208731 109209670 109214392 109222069
INI: 109151261
ITR: 116018951 116020026
OEU: 111397003 111401399
SSPL: 121769123
SHIS: 125205603 125208429
APAN: 127257822 127258364
HAN: 110896133 110896135 110904031 110904034 110904035 110930525
ECAD: 122580503 122603312 122603728 122604752 122605464 122605846
LSV: 111876447 111876451 111915138
CCAV: 112511566 112512108 112512116 112512670 112524614 112525570
CSIN: 114318634 114318645 114318657
RVL: 131303768
AEW: 130768412
MOF: 131168094 131168196
NNU: 104587776 104595421 104595431
MING: 122081730 122081742 122094355
TSS: 122638333 122638340
PSOM: 113275454 113277622 113319234
OSA: 4352160
OGL: 127757523
ATS: 109758011
TDC: 119326475
TAES: 101290585 123072527 123072528
TUA: 125552198
ZMA: 101027254
PVIR: 120643818 120685624
PHAI: 112903103
PDA: 103698676 103714427
EGU: 105056278 105056286
MUS: 103973892 103998463
ZOF: 122050328 122051689 122056220
MSIN: 131218050 131218908 131218912 131218913 131235421
NCOL: 116249773
ATR: 18427569 18428104
SMO: SELMODRAFT_229898
PPP: 112278006
 » show all
Reference
1
  Authors
Akakabe Y, Matsui K, Kajiwara T.
  Title
Enantioselective alpha-hydroperoxylation of long-chain fatty acids with crude enzyme of marine green alga Ulva pertusa.
  Journal
Tetrahedron Lett 40:1137-1140 (1999)
Reference
2  [PMID:10455113]
  Authors
Hamberg M, Sanz A, Castresana C
  Title
alpha-oxidation of fatty acids in higher plants. Identification of a pathogen-inducible oxygenase (piox) as an alpha-dioxygenase and biosynthesis of 2-hydroperoxylinolenic acid.
  Journal
J Biol Chem 274:24503-13 (1999)
DOI:10.1074/jbc.274.35.24503
Reference
3  [PMID:10938370]
  Authors
Saffert A, Hartmann-Schreier J, Schon A, Schreier P.
  Title
A dual function alpha-dioxygenase-peroxidase and NAD(+) oxidoreductase active enzyme from germinating pea rationalizing alpha-oxidation of fatty acids in plants.
  Journal
Plant Physiol 123:1545-52 (2000)
DOI:10.1104/pp.123.4.1545
Reference
4  [PMID:11909851]
  Authors
Koeduka T, Matsui K, Akakabe Y, Kajiwara T.
  Title
Catalytic properties of rice alpha-oxygenase. A comparison with mammalian prostaglandin H synthases.
  Journal
J Biol Chem 277:22648-55 (2002)
DOI:10.1074/jbc.M110420200
  Sequence
[osa:4352160]
Reference
5  [PMID:15100225]
  Authors
Liu W, Rogge CE, Bambai B, Palmer G, Tsai AL, Kulmacz RJ.
  Title
Characterization of the heme environment in Arabidopsis thaliana fatty acid alpha-dioxygenase-1.
  Journal
J Biol Chem 279:29805-15 (2004)
DOI:10.1074/jbc.M401779200
Reference
6  [PMID:18760499]
  Authors
Meisner AK, Saffert A, Schreier P, Schon A.
  Title
Fatty acid alpha-dioxygenase from Pisum sativum: temporal and spatial regulation during germination and plant development.
  Journal
J Plant Physiol 166:333-43 (2009)
DOI:10.1016/j.jplph.2008.05.009
  Sequence
[ag:CAH05011]
Other DBs
ExplorEnz - The Enzyme Database: 1.13.11.92
IUBMB Enzyme Nomenclature: 1.13.11.92
ExPASy - ENZYME nomenclature database: 1.13.11.92
BRENDA, the Enzyme Database: 1.13.11.92
LinkDB

KEGG   REACTION: R12775
Entry
R12775                      Reaction                               
Definition
(9Z,12Z,15Z)-Octadecatrienoic acid + Oxygen <=> 2(R)-HPOT
Equation
C06427 + C00007 <=> C16341
Enzyme
1.13.11.92
Pathway
rn00592  alpha-Linolenic acid metabolism
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.13  Acting on single donors with incorporation of molecular oxygen (oxygenases)
   1.13.11  With incorporation of two atoms of oxygen
    1.13.11.92
     R12775  (9Z,12Z,15Z)-Octadecatrienoic acid + Oxygen <=> 2(R)-HPOT
IUBMB reaction hierarchy [BR:br08202]
 1. Oxidoreductase reactions
  1.13.11.92
   R12771  Fatty acid <=> (2R)-2-Hydroperoxyfatty acid
    R12775  (9Z,12Z,15Z)-Octadecatrienoic acid <=> 2(R)-HPOT
Orthology
K10529  fatty acid alpha-dioxygenase [EC:1.13.11.92]
Other DBs
RHEA: 16332
LinkDB

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