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Information on EC 1.14.14.156 - tryptophan N-monooxygenase

for references in articles please use BRENDA:EC1.14.14.156

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IUBMB Comments

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.

The enzyme appears in viruses and cellular organisms

Synonyms
cyp79b2, cyp79b3, cyp79b1, more

REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (E)-indol-3-ylacetaldoxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
show the reaction diagram
overall reaction
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L-tryptophan + [reduced NADPH-hemoprotein reductase] + O2 = N-hydroxy-L-tryptophan + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
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N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O
show the reaction diagram
(1c)
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N-hydroxy-L-tryptophan + [reduced NADPH-hemoprotein reductase] + O2 = N,N-dihydroxy-L-tryptophan + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1b)
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