KEGG   ENZYME: 1.14.14.43Help
Entry
EC 1.14.14.43               Enzyme                                 

Name
(methylsulfanyl)alkanaldoxime N-monooxygenase;
CYP83A1 (gene name);
(methylthio)alkanaldoxime N-monooxygenase;
(E)-omega-(methylthio)alkananaldoxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
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
(E)-omega-(methylsulfanyl)alkananal oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
an (E)-omega-(methylsulfanyl)alkanal oxime + [reduced NADPH---hemoprotein reductase] + glutathione + O2 = an S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11650];
(1a) an (E)-omega-(methylsulfanyl)alkanal oxime + [reduced NADPH---hemoprotein reductase] + O2 = a 1-(methylsulfanyl)-4-aci-nitroalkane + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11651];
(1b) a 1-(methylsulfanyl)-4-aci-nitroalkane + glutathione = an S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione + H2O [RN:R11652]
Reaction(KEGG)
Substrate
(E)-omega-(methylsulfanyl)alkanal oxime [CPD:C21535];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
glutathione [CPD:C00051];
O2 [CPD:C00007];
1-(methylsulfanyl)-4-aci-nitroalkane [CPD:C21538]
Product
S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione [CPD:C21539];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
1-(methylsulfanyl)-4-aci-nitroalkane [CPD:C21538]
Comment
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of glucosinolates in plants. The enzyme catalyses an N-hydroxylation of the E isomer of omega-(methylsulfanyl)alkanal oximes, forming an aci-nitro intermediate that reacts non-enzymically with glutathione to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates. In the absence of a thiol compound, the enzyme is suicidal, probably due to interaction of the reactive aci-nitro intermediate with active site residues.
History
EC 1.14.14.43 created 2017
Pathway
ec00966  Glucosinolate biosynthesis
Orthology
K12156  (methylthio)alkanaldoxime N-monooxygenase
Genes
ATH: AT4G13770(CYP83A1)
ALY: ARALYDRAFT_493537
CRB: 17877864
CSAT: 104719080
EUS: EUTSA_v10024982mg
BRP: 103863599(CYP83A1) 103865912(CYP83A1-2)
BNA: 106430121 106447562
BOE: 106339606 106342466
THJ: 104806927 104813171
Taxonomy
Reference
1  [PMID:11158532]
  Authors
Bak S, Tax FE, Feldmann KA, Galbraith DW, Feyereisen R
  Title
CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis.
  Journal
Plant Cell 13:101-11 (2001)
Reference
2  [PMID:12970475]
  Authors
Naur P, Petersen BL, Mikkelsen MD, Bak S, Rasmussen H, Olsen CE, Halkier BA.
  Title
CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis.
  Journal
Plant Physiol 133:63-72 (2003)
DOI:10.1104/pp.102.019240
  Sequence
[ath:AT4G13770]
Reference
3  [PMID:26361733]
  Authors
Clausen M, Kannangara RM, Olsen CE, Blomstedt CK, Gleadow RM, Jorgensen K, Bak S, Motawie MS, Moller BL
  Title
The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.
  Journal
Plant J 84:558-73 (2015)
DOI:10.1111/tpj.13023
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.43
IUBMB Enzyme Nomenclature: 1.14.14.43
ExPASy - ENZYME nomenclature database: 1.14.14.43
BRENDA, the Enzyme Database: 1.14.14.43

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