Information on EC 1.1.3.47 - 5-(hydroxymethyl)furfural oxidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.3.47
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RECOMMENDED NAME
GeneOntology No.
5-(hydroxymethyl)furfural oxidase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
5-(dihydroxymethyl)furan-2-carbaldehyde + O2 = 5-formylfuran-2-carboxylate + H2O2
show the reaction diagram
(1c)
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5-(dihydroxymethyl)furan-2-carboxylate + O2 = furan-2,5-dicarboxylate + H2O2
show the reaction diagram
(1e)
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5-(hydroxymethyl)furfural + 3 O2 + 2 H2O = furan-2,5-dicarboxylate + 3 H2O2
show the reaction diagram
overall reaction
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5-(hydroxymethyl)furfural + O2 = furan-2,5-dicarbaldehyde + H2O2
show the reaction diagram
(1a)
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5-formylfuran-2-carboxylate + H2O = 5-(dihydroxymethyl)furan-2-carboxylate
show the reaction diagram
(1d), spontaneous
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furan-2,5-dicarbaldehyde + H2O = 5-(dihydroxymethyl)furan-2-carbaldehyde
show the reaction diagram
(1b), spontaneous
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Furfural degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
5-(hydroxymethyl)furfural:oxygen oxidoreductase
The enzyme, characterized from the bacterium Methylovorus sp. strain MP688, is involved in the degradation and detoxification of 5-(hydroxymethyl)furfural. The enzyme acts only on alcohol groups and requires the spontaneous hydration of aldehyde groups for their oxidation [3]. The enzyme has a broad substrate range that overlaps with EC 1.1.3.7, aryl-alcohol oxidase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
mutants with a disrupted hmfH gene accumulate 5-hydroxymethylfuroic acid when cultured in the presence of 5-(hydroxymethyl)furfural
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-(hydroxymethyl)benzaldehyde + O2 + H2O
?
show the reaction diagram
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-
-
?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
show the reaction diagram
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
show the reaction diagram
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
show the reaction diagram
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
show the reaction diagram
terephthaldehyde + O2 + H2O
?
show the reaction diagram
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?
additional information
?
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the enzyme has a broad substrate range that overlaps with EC 1.1.3.7, aryl-alcohol oxidase
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
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the flavin cofactor is dissociable
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.15
4-(Hydroxymethyl)benzaldehyde
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pH 7.0, 25C
1.4
5-(hydroxymethyl)furfural
1.7
furan-2,5-dicarbaldehyde
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pH 7.0, 25C
0.085
terephthaldehyde
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pH 7.0, 25C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.6
4-(Hydroxymethyl)benzaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
9.9
5-(hydroxymethyl)furfural
1.6
furan-2,5-dicarbaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
1.3
terephthaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
57
4-(Hydroxymethyl)benzaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
91615
7 - 7.1
5-(hydroxymethyl)furfural
196614
0.94
furan-2,5-dicarbaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
196623
15
terephthaldehyde
Methylovorus sp. MP688
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pH 7.0, 25C
197626
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Methylovorus sp. (strain MP688)
Methylovorus sp. (strain MP688)
Methylovorus sp. (strain MP688)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70000
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x * 70000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 70000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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when the structural genes of the furfural catabolic pathway are expressed in a heterologous host, Pseudomonas putida S12, they yield a strain capable of utilizing 5-(hydroxymethyl)furfural and furfural as sole carbon sources
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H467A
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catalysis of the mutant enzyme is severely reduced compared to that of the wild-type enzyme. With vanillyl alcohol as the substrate, the kcat value of the mutant enzyme is 4400 times lower than that of the wild-type enzyme
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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biocatalytic production of furan-2,5-dicarboxylate, a biobased platform chemical for the production of polymers