KEGG   ENZYME: 1.14.14.42Help
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
BRITE hierarchy
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)
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)
CRB: 17900662
CSAT: 104755961
EUS: EUTSA_v10007301mg
BRP: 103872429
BNA: 106367453
BOE: 106343089
RSZ: 108812420
THJ: 104812394
Taxonomy
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
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

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