KEGG   ORTHOLOGY: K12154
Entry
K12154                      KO                                     
Symbol
CYP79F1
Name
homomethionine N-monooxygenase [EC:1.14.14.42]
Pathway
map00966  Glucosinolate biosynthesis
map01110  Biosynthesis of secondary metabolites
map01210  2-Oxocarboxylic acid metabolism
Reaction
R08665  homomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
R08670  dihomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
R08672  trihomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
R08673  tetrahomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
R08674  pentahomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
R08675  hexahomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K12154  CYP79F1; homomethionine N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K12154  CYP79F1; homomethionine N-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.42  homomethionine N-monooxygenase
     K12154  CYP79F1; homomethionine N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K12154  CYP79F1; homomethionine N-monooxygenase
Genes
ATH: AT1G16410(CYP79F1)
ALY: 9328969
CRB: 17897995 17900662
CSAT: 104740326 104743340 104755961 104755962 104775479 104775492
EUS: EUTSA_v10007301mg
BRP: 103872429
BNA: 106346773 106367453
BOE: 106343089
RSZ: 108812420
Reference
PMID:11133994
  Authors
Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA
  Title
Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates.
  Journal
J Biol Chem 276:11078-85 (2001)
DOI:10.1074/jbc.M010123200
  Sequence
[ath:AT1G16410]
LinkDB

KEGG   ENZYME: 1.14.14.42
Entry
EC 1.14.14.42               Enzyme                                 
Name
homomethionine N-monooxygenase;
CYP79F1 (gene name);
CYP79F2 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
L-polyhomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
Reaction(IUBMB)
an L-polyhomomethionine + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = an (E)-omega-(methylsulfanyl)alkanal oxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R11646];
(1a) an L-polyhomomethionine + [reduced NADPH---hemoprotein reductase] + O2 = an L-N-hydroxypolyhomomethionine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11647];
(1b) an L-N-hydroxypolyhomomethionine + [reduced NADPH---hemoprotein reductase] + O2 = an L-N,N-dihydroxypolyhomomethionine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11648];
(1c) an L-N,N-dihydroxypolyhomomethionine = an (E)-omega-(methylsulfanyl)alkanal oxime + CO2 + H2O [RN:R11649]
Reaction(KEGG)
R11646 > R08665 R08670 R08672 R08673 R08674 R08675;
R11647 R11648 R11649
Substrate
L-polyhomomethionine [CPD:C21534];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
L-N-hydroxypolyhomomethionine [CPD:C21536];
L-N,N-dihydroxypolyhomomethionine [CPD:C21537]
Product
(E)-omega-(methylsulfanyl)alkanal oxime [CPD:C21535];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
L-N-hydroxypolyhomomethionine [CPD:C21536];
L-N,N-dihydroxypolyhomomethionine [CPD:C21537]
Comment
This plant cytochrome P-450 (heme thiolate) enzyme is involved in methionine-derived aliphatic glucosinolates biosynthesis. It catalyses two successive N-hydroxylations, which are followed by dehydration and decarboxylation. CYP79F1 from Arabidopsis thaliana can metabolize mono-, di-, tri-, tetra-, penta-, and hexahomomethionine to their corresponding aldoximes, while CYP79F2 from the same plant can only metabolize penta- and hexahomomethionine.
History
EC 1.14.14.42 created 2017
Pathway
ec00966  Glucosinolate biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K12154  homomethionine N-monooxygenase
K12155  homomethionine N-monooxygenase
Genes
ATH: AT1G16400(CYP79F2) AT1G16410(CYP79F1)
ALY: 9326225 9328969
CRB: 17897995 17900662
CSAT: 104740326 104743340 104755961 104755962 104775479 104775492
EUS: EUTSA_v10007301mg
BRP: 103872429
BNA: 106346773 106367453
BOE: 106343089
RSZ: 108812420
Reference
1  [PMID:11133994]
  Authors
Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA
  Title
Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates.
  Journal
J Biol Chem 276:11078-85 (2001)
DOI:10.1074/jbc.M010123200
Reference
2  [PMID:12609033]
  Authors
Chen S, Glawischnig E, Jorgensen K, Naur P, Jorgensen B, Olsen CE, Hansen CH, Rasmussen H, Pickett JA, Halkier BA
  Title
CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis.
  Journal
Plant J 33:923-37 (2003)
DOI:10.1046/j.1365-313X.2003.01679.x
  Sequence
[ath:AT1G16410 AT1G16400]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.42
IUBMB Enzyme Nomenclature: 1.14.14.42
ExPASy - ENZYME nomenclature database: 1.14.14.42
BRENDA, the Enzyme Database: 1.14.14.42
LinkDB

KEGG   REACTION: R08670
Entry
R08670                      Reaction                               
Name
dihomomethionine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase
Definition
Dihomomethionine + 2 [Reduced NADPH---hemoprotein reductase] + 2 Oxygen <=> 5-Methylthiopentanaldoxime + 2 [Oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O
Equation
C17217 + 2 C03024 + 2 C00007 <=> C17245 + 2 C03161 + C00011 + 3 C00001
Comment
multi-step reaction (similar to R10671, R00730+R04460+R07190)
Reaction class
RC02295  C17217_C17245
Enzyme
1.14.14.42
Pathway
rn00966  Glucosinolate biosynthesis
rn01210  2-Oxocarboxylic acid metabolism
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.42
     R08670  Dihomomethionine + 2 [Reduced NADPH---hemoprotein reductase] + 2 Oxygen <=> 5-Methylthiopentanaldoxime + 2 [Oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O
IUBMB reaction hierarchy [BR:br08202]
 1. Oxidoreductase reactions
  1.14.14.42
   R11646  L-Polyhomomethionine <=> omega-(Methylthio)-(E)-alkanal oxime
    R08670  Dihomomethionine <=> 5-Methylthiopentanaldoxime
Orthology
K12154  homomethionine N-monooxygenase [EC:1.14.14.42]
Other DBs
RHEA: 32722
LinkDB

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