Phenylalanine N-monooxygenase

Phenylalanine N-monooxygenase
Identifiers
EC no.1.14.14.40
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
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PMCarticles
PubMedarticles
NCBIproteins

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:

2D representation of the chemical structure of phenylalanine .
phenylalanine
+ 2 NADPH
+ 2 H+
 
 
2 O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
N,N-dihydroxy-L-phenylalanine
+ 2 NADP+
 
 
 
CO2 + H2O
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27120792.
(E)-phenylacetaldoxime

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

  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. ↑ Enzyme 1.14.14.40 at KEGG Pathway Database.
  3. ↑ 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.
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