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Information on EC 1.14.99.46 - pyrimidine oxygenase and Organism(s) Escherichia coli and UniProt Accession P75898

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EC Tree
IUBMB 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.
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This record set is specific for:
Escherichia coli
UNIPROT: P75898
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The taxonomic range for the selected organisms is: Escherichia coli
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
uracil
+
FMNH2
+
O2
+
NADH
=
(Z)-3-ureidoacrylate
+
H2O
+
FMN
+
NAD+
+
H+
+
+
+
=
(Z)-3-ureidoacrylate
+
+
+
+
thymine
+
FMNH2
+
O2
+
NADH
=
(Z)-2-methylureidoacrylate
+
H2O
+
FMN
+
NAD+
+
H+
+
+
+
=
(Z)-2-methylureidoacrylate
+
+
+
+
Synonyms
RutA, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
RutA
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
uracil,FMNH2:oxygen oxidoreductase (uracil hydroxylating, ring-opening)
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.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
thymine + FMNH2 + O2
(Z)-2-methylureidoacrylate peracid + FMN
show the reaction diagram
-
-
-
?
uracil + FMNH2 + O2
(Z)-3-ureidoacrylate peracid + FMN
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
thymine + FMNH2 + O2
(Z)-2-methylureidoacrylate peracid + FMN
show the reaction diagram
-
-
-
?
uracil + FMNH2 + O2
(Z)-3-ureidoacrylate peracid + FMN
show the reaction diagram
-
-
-
?
additional information
?
-
the pyrimidine ring is cleaved directly by adding a pair of oxygen atoms and producing ureidoacrylate peracid. This odd metabolite, a strong and highly toxic oxidizing agent, is reduced spontaneously, albeit slowly, to ureidoacrylate
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
FAD works much less well than FMN
additional information
RutA-catalyzed reduction or reduction by excess NADH or DTT in the reaction buffer
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8.2
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
assay at room temperature
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
RutA has a central role in the Rut pathway, which is composed of seven proteins, all of which are required by Escherichia coli K-12 to grow on uracil as the sole nitrogen source
additional information
the Rut pathway degrades exogenous pyrimidines as the sole nitrogen source at room temperature but not at 37°C, a restriction that is apparently a consequence of an inadequate ability to remove toxic malonic semialdehyde at the higher temperature, RutE/YdfG function. The catabolic pathway is highly expressed even in the absence of exogenous substrate and at 37°C
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant RutA, X-ray diffraction structure determination and analysis at 1.8 A resolution
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged RutA from ASKA strain JW0997 by nickel affinity chromatography
recombinant His-tagged RutA from Escherichia coli strain BL21 by nickel affinity chromatography to homogeneity
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene rutA, expression of the His-tagged enzyme in Escherichia coli strain BL21, co-expression with rutF
gene rutA, recombinant overexpression of His-tagged RutA in ASKA strain JW0997
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Mukherjee, T.; Zhang, Y.; Abdelwahed, S.; Ealick, S.E.; Begley, T.P.
Catalysis of a flavoenzyme-mediated amide hydrolysis
J. Am. Chem. Soc.
132
5550-5551
2010
Escherichia coli (P75898)
Manually annotated by BRENDA team
Parales, R.; Ingraham, J.
The surprising Rut pathway: An unexpected way to derive nitrogen from pyrimidines
J. Bacteriol.
192
4086-4088
2010
Escherichia coli (P75898)
Manually annotated by BRENDA team
Kim, K.S.; Pelton, J.G.; Inwood, W.B.; Andersen, U.; Kustu, S.; Wemmer, D.E.
The Rut pathway for pyrimidine degradation: novel chemistry and toxicity problems
J. Bacteriol.
192
4089-4102
2010
Escherichia coli (P75898)
Manually annotated by BRENDA team