KEGG   ENZYME: 1.14.13.125Help
Entry
EC 1.14.13.125              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 NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
L-tryptophan,NADPH:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
L-tryptophan + 2 O2 + 2 NADPH + 2 H+ = (E)-indol-3-ylacetaldoxime + 2 NADP+ + CO2 + 3 H2O (overall reaction) [RN:R08160];
(1a) L-tryptophan + O2 + NADPH + H+ = N-hydroxy-L-tryptophan + NADP+ + H2O [RN:R09583];
(1b) N-hydroxy-L-tryptophan + O2 + NADPH + H+ = N,N-dihydroxy-L-tryptophan + NADP+ + H2O [RN:R09584];
(1c) N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O [RN:R09585]
Reaction(KEGG)
Substrate
L-tryptophan [CPD:C00078];
O2 [CPD:C00007];
NADPH [CPD:C00005];
H+ [CPD:C00080];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]
Product
(E)-indol-3-ylacetaldoxime [CPD:C02937];
NADP+ [CPD:C00006];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]
Comment
A heme-thiolate protein (P-450). This enzyme catalyses two successive N-hydroxylations of L-tryptophan, the first steps in the biosynthesis of the 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 the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The product, (E)-indol-3-ylacetaldoxime, undergoes a spontaneous isomerization to the (Z) form.
History
EC 1.14.13.125 created 2011
Pathway
Tryptophan metabolism
Glucosinolate biosynthesis
Biosynthesis of secondary metabolites
Orthology
K11812  
tryptophan N-monooxygenase
K11813  
tryptophan N-monooxygenase
Genes
ATH: 
AT2G22330(CYP79B3) AT4G39950(CYP79B2)
ALY: 
CRB: 
EUS: 
Taxonomy
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 (2000) 33712-7.
  Organism
Arabidopsis catalyzes
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 (2000) 2379-84.
  Organism
Arabidopsis cytochrome
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 (2002) 3100-12.
  Organism
Arabidopsis thaliana [GN:ath]
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 (2003) 235-41.
  Organism
Sinapis alba
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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