+ 2 NADPH
+ 2 H+
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] It catalyses the following sequence of chemical reactions:
| 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 | ||||||||
| |||||||||
-phenylacetaldoxime.svg)
The enzyme uses molecular oxygen and reduced nicotinamide adenine dinucleotide phosphate (NADPH) to convert L-phenylalanine first to its N-hydroxy derivative and then to N,N-dihydroxy-L-phenylalanine. This compound is unstable and loses carbon dioxide and water to give the (E) isomer of phenylacetaldoxime.[2]
Phenylalanine N-monooxygenase is a cytochrome P450 protein containing heme. It is part of the pathway in plants which converts phenylalanine to the glucosinolate, glucotropaeolin, which contributes to the characteristic flavor of brassicas.[3]
References
edit- ↑ 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.
- ↑ Enzyme 1.14.14.40 at KEGG Pathway Database.
- ↑ 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
edit- Phenylalanine+N-monooxygenase at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
