Phenylalanine N-monooxygenase

Phenylalanine N-monooxygenase
Identifiers
EC no.	1.14.14.40
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

Phenylalanine N-monooxygenase (EC 1.14.14.40, phenylalanine N-hydroxylase, CYP79A2) is an enzyme with systematic name L-phenylalanine,NADPH:oxygen oxidoreductase (N-hydroxylating). ^[1] This enzyme catalyses the following chemical reaction

L-phenylalanine + 2 O₂ + 2 NADPH + 2 H⁺${\displaystyle \rightleftharpoons }$ (E)-phenylacetaldoxime + 2 NADP⁺ + CO₂ + 3 H₂O (overall reaction)

(1a) L-phenylalanine + O₂ + NADPH + H⁺${\displaystyle \rightleftharpoons }$ N-hydroxy-L-phenylalanine + NADP⁺ + H₂O:

(1b) N-hydroxy-L-phenylalanine + O₂ + NADPH + H⁺${\displaystyle \rightleftharpoons }$ N,N-dihydroxy-L-phenylalanine + NADP⁺ + H₂O

(1c) N,N-dihydroxy-L-phenylalanine ${\displaystyle \rightleftharpoons }$ (E)-phenylacetaldoxime + CO₂ + H₂O

Phenylalanine N-monooxygenase is a heme-thiolate protein (P-450). It is part of the pathway in plants which converts phenylalanine to the glucosinolate, glucotropaeolin, which contributes to the characteristic flavor of brassicas. ^[2]

References

1. Wittstock U, Halkier BA (May 2000). "Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate". The Journal of Biological Chemistry. 275 (19): 14659–66. doi: 10.1074/jbc.275.19.14659 . PMID   10799553.
2. Blažević I, Montaut S, Burčul F, Olsen CE, Burow M, Rollin P, Agerbirk N (2020). "Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants" (PDF). Phytochemistry. 169: 112100. Bibcode:2020PChem.169k2100B. doi: 10.1016/j.phytochem.2019.112100 . PMID   31771793. S2CID   208318505.

External links

• Phenylalanine+N-monooxygenase at the U.S. National Library of Medicine Medical Subject Headings (MeSH)