Tryptophan N-monooxygenase

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Tryptophan N-monooxygenase
Identifiers
EC no. 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

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+ (E)-indol-3-ylacetaldoxime + 2 NADP+ + CO2 + 3 H2O (overall reaction)
(1a) L-tryptophan + O2 + NADPH + H+ N-hydroxy-L-tryptophan + NADP+ + H2O
(1b) N-hydroxy-L-tryptophan + O2 + NADPH + H+ N,N-dihydroxy-L-tryptophan + NADP+ + H2O
(1c) N,N-dihydroxy-L-tryptophan (E)-indol-3-ylacetaldoxime + CO2 + H2O

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

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References

  1. Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA (October 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". The Journal of Biological Chemistry. 275 (43): 33712–7. doi: 10.1074/jbc.M001667200 . PMID   10922360.
  2. Hull AK, Vij R, Celenza JL (February 2000). "Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 97 (5): 2379–84. doi: 10.1073/pnas.040569997 . PMC   15809 . PMID   10681464.
  3. Zhao Y, Hull AK, Gupta NR, Goss KA, Alonso J, Ecker JR, Normanly J, Chory J, Celenza JL (December 2002). "Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3". Genes & Development. 16 (23): 3100–12. doi:10.1101/gad.1035402. PMC   187496 . PMID   12464638.
  4. Naur P, Hansen CH, Bak S, Hansen BG, Jensen NB, Nielsen HL, Halkier BA (January 2003). "CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime". Archives of Biochemistry and Biophysics. 409 (1): 235–41. doi:10.1016/s0003-9861(02)00567-2. PMID   12464264.