Tryptophan N-monooxygenase

Tryptophan N-monooxygenase
Identifiers
EC number	1.14.13.125
Databases
IntEnz	IntEnz view
BRENDA	BRENDA entry
ExPASy	NiceZyme view
KEGG	KEGG entry
MetaCyc	metabolic pathway
PRIAM	profile
PDB structures	RCSB PDB PDBe PDBsum
Search PMC articles PubMed articles NCBI proteins

Tryptophan N-monooxygenase (EC 1.14.13.125, tryptophan N-hydroxylase, CYP79B1, CYP79B2, CYP79B3) is an enzyme with systematic name L-tryptophan,NADPH:oxygen oxidoreductase (N-hydroxylating).^[1][2][3][4] This enzyme catalyses the following chemical reaction

L-tryptophan + 2 O₂ + 2 NADPH + 2 H⁺ $\rightleftharpoons$ (E)-indol-3-ylacetaldoxime + 2 NADP⁺ + CO₂ + 3 H₂O (overall reaction)

(1a) L-tryptophan + O₂ + NADPH + H⁺ $\rightleftharpoons$ N-hydroxy-L-tryptophan + NADP⁺ + H₂O

(1b) N-hydroxy-L-tryptophan + O₂ + NADPH + H⁺ $\rightleftharpoons$ N,N-dihydroxy-L-tryptophan + NADP⁺ + H₂O

(1c) N,N-dihydroxy-L-tryptophan $\rightleftharpoons$ (E)-indol-3-ylacetaldoxime + CO₂ + H₂O

Tryptophan N-monooxygenase is a heme-thiolate protein (P-450).

References

1. Mikkelsen, M.D., Hansen, C.H., Wittstock, U. and Halkier, B.A. (2000). "Cytochrome P₄₅₀ CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid". J. Biol. Chem. 275 (43): 33712–33717. doi:10.1074/jbc.M001667200. PMID 10922360.
2. Hull, A.K., Vij, R. and Celenza, J.L. (2000). "Arabidopsis cytochrome P₄₅₀s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis". Proc. Natl. Acad. Sci. USA 97 (5): 2379–2384. doi:10.1073/pnas.040569997. PMC 15809. PMID 10681464.
3. Zhao, Y., Hull, A.K., Gupta, N.R., Goss, K.A., Alonso, J., Ecker, J.R., Normanly, J., Chory, J. and Celenza, J.L. (2002). "Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P₄₅₀s CYP79B2 and CYP79B3". Genes Dev. 16 (23): 3100–3112. doi:10.1101/gad.1035402. PMC 187496. PMID 12464638.
4. Naur, P., Hansen, C.H., Bak, S., Hansen, B.G., Jensen, N.B., Nielsen, H.L. and Halkier, B.A. (2003). "CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime". Arch. Biochem. Biophys. 409 (1): 235–241. doi:10.1016/s0003-9861(02)00567-2. PMID 12464264.

External links

• Tryptophan N-monooxygenase at the US National Library of Medicine Medical Subject Headings (MeSH)