KEGG   ORTHOLOGY: K11812
Entry
K11812                      KO                                     

Name
CYP79B1_2
Definition
tryptophan N-monooxygenase [EC:1.14.14.156]
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
    K11812  CYP79B1_2; tryptophan N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K11812  CYP79B1_2; tryptophan N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K11812  CYP79B1_2; tryptophan 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
    1.14.14.156  tryptophan N-monooxygenase
     K11812  CYP79B1_2; tryptophan N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K11812  CYP79B1_2; tryptophan N-monooxygenase
Other DBs
RN: R08160
Genes
ATH: AT4G39950(CYP79B2)
ALY: 9302968
CRB: 17879334
CSAT: 104716281 104720922 104729322 104729349
EUS: EUTSA_v10000278mg EUTSA_v10024861mg
BRP: 103835554 103853878 103862605
BNA: 106361376 106382592 106410467 106426528 106439341 106441279
BOE: 106301717 106302779 106330945
RSZ: 108818790 108830725 108855674
THJ: 104804164 104807687
Reference
  Authors
Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA
  Title
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid.
  Journal
J Biol Chem 275:33712-7 (2000)
DOI:10.1074/jbc.M001667200
  Sequence
[ath:AT4G39950]
Reference
PMID:12464264 (CYP79B5)
  Authors
Naur P, Hansen CH, Bak S, Hansen BG, Jensen NB, Nielsen HL, Halkier BA
  Title
CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime.
  Journal
Arch Biochem Biophys 409:235-41 (2003)
DOI:10.1016/S0003-9861(02)00567-2
  Sequence
[brp:103853878]

KEGG   ORTHOLOGY: K11813
Entry
K11813                      KO                                     

Name
CYP79B3
Definition
tryptophan N-monooxygenase [EC:1.14.14.156]
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
    K11813  CYP79B3; tryptophan N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K11813  CYP79B3; tryptophan N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K11813  CYP79B3; tryptophan 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
    1.14.14.156  tryptophan N-monooxygenase
     K11813  CYP79B3; tryptophan N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K11813  CYP79B3; tryptophan N-monooxygenase
Other DBs
RN: R08160
Genes
ATH: AT2G22330(CYP79B3)
ALY: 9314677
CRB: 17889834
CSAT: 104702772 104713678 104751874
EUS: EUTSA_v10000114mg
BRP: 103864341
BNA: 106446405
BOE: 106337668
RSZ: 108839219 108850755 108851800
THJ: 104824879
Reference
  Authors
Hull AK, Vij R, Celenza JL
  Title
Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis.
  Journal
Proc Natl Acad Sci U S A 97:2379-84 (2000)
DOI:10.1073/pnas.040569997
  Sequence
[ath:AT2G22330]

KEGG   ENZYME: 1.14.14.156
Entry
EC 1.14.14.156              Enzyme                                 

Name
tryptophan N-monooxygenase;
tryptophan N-hydroxylase;
CYP79B1;
CYP79B2;
CYP79B3
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-tryptophan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
L-tryptophan + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = (E)-indol-3-ylacetaldoxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R08160];
(1a) L-tryptophan + [reduced NADPH---hemoprotein reductase] + O2 = N-hydroxy-L-tryptophan + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09583];
(1b) N-hydroxy-L-tryptophan + [reduced NADPH---hemoprotein reductase] + O2 = N,N-dihydroxy-L-tryptophan + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09584];
(1c) N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O [RN:R09585]
Reaction(KEGG)
Substrate
L-tryptophan [CPD:C00078];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]
Product
(E)-indol-3-ylacetaldoxime [CPD:C02937];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]
Comment
A cytochrome P-450 (heme-thiolate) protein from the plant Arabidopsis thaliana. This enzyme catalyses two successive N-hydroxylations of L-tryptophan, the first steps in the biosynthesis of both auxin and the indole alkaloid phytoalexin camalexin. The product of the two hydroxylations, N,N-dihydroxy-L-tryptophan, is extremely labile and dehydrates spontaneously. The dehydrated product is then subject to a decarboxylation that produces an oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme.
History
EC 1.14.14.156 created 2011 as EC 1.14.13.125, transferred 2018 to EC 1.14.14.156
Pathway
ec00380  Tryptophan metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K11812  tryptophan N-monooxygenase
K11813  tryptophan N-monooxygenase
Genes
ATH: AT2G22330(CYP79B3) AT4G39950(CYP79B2)
ALY: 9302968 9314677
CRB: 17879334 17889834
CSAT: 104702772 104713678 104716281 104720922 104729322 104729349 104751874
EUS: EUTSA_v10000114mg EUTSA_v10000278mg EUTSA_v10024861mg
BRP: 103835554 103853878 103862605 103864341
BNA: 106361376 106382592 106410467 106426528 106439341 106441279 106446405
BOE: 106301717 106302779 106330945 106337668
RSZ: 108818790 108830725 108839219 108850755 108851800 108855674
THJ: 104804164 104807687 104824879
Reference
1  [PMID:10922360]
  Authors
Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA
  Title
Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid.
  Journal
J Biol Chem 275:33712-7 (2000)
DOI:10.1074/jbc.M001667200
  Sequence
[ath:AT4G39950]
Reference
2  [PMID:10681464]
  Authors
Hull AK, Vij R, Celenza JL
  Title
Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis.
  Journal
Proc Natl Acad Sci U S A 97:2379-84 (2000)
DOI:10.1073/pnas.040569997
  Sequence
Reference
3  [PMID:12464638]
  Authors
Zhao Y, Hull AK, Gupta NR, Goss KA, Alonso J, Ecker JR, Normanly J, Chory J, Celenza JL
  Title
Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s  CYP79B2 and CYP79B3.
  Journal
Genes Dev 16:3100-12 (2002)
DOI:10.1101/gad.1035402
Reference
4  [PMID:12464264]
  Authors
Naur P, Hansen CH, Bak S, Hansen BG, Jensen NB, Nielsen HL, Halkier BA
  Title
CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime.
  Journal
Arch Biochem Biophys 409:235-41 (2003)
DOI:10.1016/S0003-9861(02)00567-2
  Sequence
[brp:103853878]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.156
IUBMB Enzyme Nomenclature: 1.14.14.156
ExPASy - ENZYME nomenclature database: 1.14.14.156
BRENDA, the Enzyme Database: 1.14.14.156

KEGG   REACTION: R08160
Entry
R08160                      Reaction                               

Name
L-tryptophan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Definition
L-Tryptophan + 2 [Reduced NADPH---hemoprotein reductase] + 2 Oxygen <=> Indole-3-acetaldehyde oxime + 2 [Oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O
Equation
C00078 + 2 C03024 + 2 C00007 <=> C02937 + 2 C03161 + C00011 + 3 C00001
Comment
three-step reaction (see R09583+R09584+R09585)
Reaction class
RC02295  C00078_C02937
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
K11812  tryptophan N-monooxygenase [EC:1.14.14.156]
K11813  tryptophan N-monooxygenase [EC:1.14.14.156]
Other DBs
RHEA: 33282

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