KEGG   ORTHOLOGY: K11818
Entry
K11818                      KO                                     

Name
CYP83B1
Definition
aromatic aldoxime N-monooxygenase [EC:1.14.14.45]
Pathway
ko00380  Tryptophan metabolism
ko00966  Glucosinolate biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01210  2-Oxocarboxylic acid metabolism
Module
M00370  Glucosinolate biosynthesis, tryptophan => glucobrassicin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09105 Amino acid metabolism
   00380 Tryptophan metabolism
    K11818  CYP83B1; aromatic aldoxime N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K11818  CYP83B1; aromatic aldoxime N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K11818  CYP83B1; aromatic aldoxime 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
    1.14.14.45  aromatic aldoxime N-monooxygenase
     K11818  CYP83B1; aromatic aldoxime N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP83 family
   K11818  CYP83B1; aromatic aldoxime N-monooxygenase
Other DBs
RN: R08168 R08653 R08659 R10670 R10672
Genes
ATH: AT4G31500(CYP83B1)
ALY: 9303371
CRB: 17879907
CSAT: 104721689 104727643 104730102
EUS: EUTSA_v10004064mg
BRP: 103833295
BNA: 106361266 106372082
BOE: 106312180
RSZ: 108829823
THJ: 104806926
CPAP: 110818289
 » show all
Reference
  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:AT4G31500]

KEGG   ENZYME: 1.14.14.45
Entry
EC 1.14.14.45               Enzyme                                 

Name
aromatic aldoxime N-monooxygenase;
CYP83B1 (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
(E)-indol-3-ylacetaldoxime,[reduced NADPH---hemoprotein reductase],glutathione:oxygen oxidoreductase (oxime-hydroxylating)
Reaction(IUBMB)
(1) (E)-indol-3-ylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + glutathione + O2 = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11734];
(1a) (E)-indol-3-ylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + O2 = 1-(1H-indol-3-yl)-2-aci-nitroethane + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11735];
(1b) 1-(1H-indol-3-yl)-2-aci-nitroethane + glutathione = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + H2O (spontaneous) [RN:R11736];
(2) (E)-phenylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + glutathione + O2 = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11737];
(2a) (E)-phenylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + O2 = 1-aci-nitro-2-phenylethane + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11738];
(2b) 1-aci-nitro-2-phenylethane + glutathione = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + H2O (spontaneous) [RN:R11739]
Reaction(KEGG)
Substrate
(E)-indol-3-ylacetaldehyde oxime;
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
glutathione [CPD:C00051];
O2 [CPD:C00007];
1-(1H-indol-3-yl)-2-aci-nitroethane [CPD:C17204];
(E)-phenylacetaldehyde oxime [CPD:C19714];
1-aci-nitro-2-phenylethane [CPD:C21623]
Product
S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione [CPD:C21620];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
1-(1H-indol-3-yl)-2-aci-nitroethane [CPD:C17204];
S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione [CPD:C21622];
1-aci-nitro-2-phenylethane [CPD:C21623]
Comment
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of glucosinolates in plants. The enzyme catalyses the N-hydroxylation of aromatic aldoximes derived from L-tryptophan, L-phenylalanine, and L-tyrosine, 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 glutathione, the enzyme is suicidal, probably due to interaction of the reactive aci-nitro compound with catalytic residues in the active site.
History
EC 1.14.14.45 created 2017
Pathway
ec00380  Tryptophan metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K11818  aromatic aldoxime N-monooxygenase
Genes
ATH: AT4G31500(CYP83B1)
ALY: 9303371
CRB: 17879907
CSAT: 104721689 104727643 104730102
EUS: EUTSA_v10004064mg
BRP: 103833295
BNA: 106361266 106372082
BOE: 106312180
RSZ: 108829823
THJ: 104806926
CPAP: 110818289
 » show all
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)
DOI:10.1105/tpc.13.1.101
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
Reference
3  [PMID:21712415]
  Authors
Geu-Flores F, Moldrup ME, Bottcher C, Olsen CE, Scheel D, Halkier BA
  Title
Cytosolic gamma-glutamyl peptidases process glutathione conjugates in the biosynthesis of glucosinolates and camalexin in Arabidopsis.
  Journal
Plant Cell 23:2456-69 (2011)
DOI:10.1105/tpc.111.083998
  Sequence
[ath:AT4G31500]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.45
IUBMB Enzyme Nomenclature: 1.14.14.45
ExPASy - ENZYME nomenclature database: 1.14.14.45
BRENDA, the Enzyme Database: 1.14.14.45

KEGG   REACTION: R08168
Entry
R08168                      Reaction                               

Name
indole-3-acetaldehyde-oxime,NADPH:oxidoreductase
Definition
Indole-3-acetaldehyde oxime + L-Cysteine + NADPH + Oxygen + H+ <=> S-(Indolylmethylthiohydroximoyl)-L-cysteine + NADP+ + 2 H2O
Equation
Comment
two-step reaction (see R08607+R08608)
Reaction class
RC00001  C00005_C00006
RC01705  C00097_C16518
RC02210  C02937_C16518
Enzyme
Pathway
rn00380  Tryptophan metabolism
rn00966  Glucosinolate biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
rn01210  2-Oxocarboxylic acid metabolism
Module
M00370  Glucosinolate biosynthesis, tryptophan => glucobrassicin
Orthology
K11818  aromatic aldoxime N-monooxygenase [EC:1.14.14.45]

DBGET integrated database retrieval system