ExplorEnz: EC 1.14.99.46

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1.14.99.46

Accepted name:

pyrimidine oxygenase

Reaction:

(1) uracil + FMNH₂ + O₂ + NADH = (Z)-3-ureidoacrylate + H₂O + FMN + NAD⁺ + H⁺ (overall reaction)
(1a) FMNH₂ + O₂ = FMN-N⁵-peroxide
(1b) uracil + FMN-N⁵-peroxide = (Z)-3-ureidoacrylate + FMN-N⁵-oxide
(1c) FMN-N⁵-oxide + NADH = FMN + H₂O + NAD⁺ + H⁺ (spontaneous)
(2) thymine + FMNH₂ + O₂ + NADH = (Z)-2-methylureidoacrylate + H₂O + FMN + NAD⁺ + H⁺ (overall reaction)
(2a) FMNH₂ + O₂ = FMN-N⁵-peroxide
(2b) thymine + FMN-N⁵-peroxide = (Z)-2-methylureidoacrylate + FMN-N⁵-oxide
(2c) FMN-N⁵-oxide + NADH = FMN + H₂O + NAD⁺ + H⁺ (spontaneous)

Glossary:

(Z)-3-ureidoacrylate = (2Z)-3-(carbamoylamino)prop-2-enoate
(Z)-2-methylureidoacrylate = (2Z)-3-(carbamoylamino)-2-methylprop-2-enoate

Other name(s):

rutA (gene name)

Systematic name:

uracil,FMNH₂:oxygen oxidoreductase (uracil hydroxylating, ring-opening)

Comments:

The enzyme participates in the Rut pyrimidine catabolic pathway. The flavin-N⁵-oxide that is formed by the enzyme reacts spontaneously with NADH to give oxidized flavin, releasing a water molecule.

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc, PDB

References:

1.	Mukherjee, T., Zhang, Y., Abdelwahed, S., Ealick, S.E. and Begley, T.P. Catalysis of a flavoenzyme-mediated amide hydrolysis. J. Am. Chem. Soc. 132 (2010) 5550–5551. [DOI] [PMID: 20369853]
2.	Kim, K.S., Pelton, J.G., Inwood, W.B., Andersen, U., Kustu, S. and Wemmer, D.E. The Rut pathway for pyrimidine degradation: novel chemistry and toxicity problems. J. Bacteriol. 192 (2010) 4089–4102. [DOI] [PMID: 20400551]
3.	Adak, S. and Begley, T.P. RutA-catalyzed oxidative cleavage of the uracil amide involves formation of a flavin-N⁵-oxide. Biochemistry 56 (2017) 3708–3709. [PMID: 28661684]
4.	Adak, S. and Begley, T.P. Flavin-N⁵-oxide: A new, catalytic motif in flavoenzymology. Arch. Biochem. Biophys. 632 (2017) 4–10. [PMID: 28784589]
5.	Matthews, A., Saleem-Batcha, R., Sanders, J.N., Stull, F., Houk, K.N. and Teufel, R. Aminoperoxide adducts expand the catalytic repertoire of flavin monooxygenases. Nat. Chem. Biol. 16 (2020) 556–563. [DOI] [PMID: 32066967]

[EC 1.14.99.46 created 2012, modified 2019]