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

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

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
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SwissProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
mutants with a disrupted hmfH gene accumulate 5-hydroxymethylfuroic acid when cultured in the presence of 5-(hydroxymethyl)furfural
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-1-phenylethanol + O2
acetophenone + H2O2
show the reaction diagram
-
-
-
-
?
(S)-1-phenylethanol + O2
acetophenone + H2O2
show the reaction diagram
-
-
-
-
?
2,5-diformylfuran + O2
2,5-furandicarboxylic acid + H2O2
show the reaction diagram
2,5-hydroxymethylfurancarboxylic acid + O2
2,5-furandicarboxylic acid + H2O2
show the reaction diagram
very low activity
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-
?
4-(hydroxymethyl)benzaldehyde + O2 + H2O
?
show the reaction diagram
-
-
-
?
4-hydroxy-3-methoxybenzyl alcohol + O2
4-hydroxy-3-methoxybenzaldehyde + H2O2
show the reaction diagram
-
-
-
-
?
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
5-formylfuran-2-carboxylate + H2O
5-(dihydroxymethyl)furan-2-carboxylate
show the reaction diagram
-
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
show the reaction diagram
5-hydroxymethylfurfural + O2
2,5-hydroxymethylfurancarboxylic acid + H2O2
show the reaction diagram
-
-
-
?
furan-2,5-dicarbaldehyde + H2O
5-(dihydroxymethyl)furan-2-carbaldehyde
show the reaction diagram
-
-
-
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?
terephthaldehyde + O2 + H2O
?
show the reaction diagram
-
-
-
?
additional information
?
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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
2,5-diformylfuran + O2
2,5-furandicarboxylic acid + H2O2
show the reaction diagram
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
-
-
-
-
?
5-formylfuran-2-carboxylate + H2O
5-(dihydroxymethyl)furan-2-carboxylate
show the reaction diagram
-
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
show the reaction diagram
furan-2,5-dicarbaldehyde + H2O
5-(dihydroxymethyl)furan-2-carbaldehyde
show the reaction diagram
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?
additional information
?
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O94219
the ability of fungal aryl-alcohol oxidase (AAO) to oxidize 5-hydroxymethylfurfural (HMF) results in almost complete conversion into 2,5-formylfurancarboxylic acid (FFCA) in a few hours. The reaction starts with alcohol oxidation, yielding 2,5-diformylfuran (DFF), which is rapidly converted into FFCA by carbonyl oxidation, most probably without leaving the enzyme active site. AAO is combined with an unspecific peroxygenase, UPO, EC 1.11.2.1, from Agrocybe aegerita for full oxidative conversion of 5-hydroxymethylfurfural in an enzymatic cascade. This peroxygenase belongs to the recently described superfamily of hemethiolate peroxidases, and is capable of incorporating peroxide-borne oxygen into diverse substrate molecules. In contrast to AAO, the UPO reaction starts with oxidation of the HMF carbonyl group, yielding 2,5-hydroxymethylfurancarboxylic, which is converted into 2,5-formylfurancarboxylic acid and some 2,5-furandicarboxylic acid
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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
20 - 98
(S)-1-phenylethanol
3.3
2,5-diformylfuran
pH 6.0, 25C
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0.15
4-(Hydroxymethyl)benzaldehyde
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pH 7.0, 25C
0.2 - 2
4-Hydroxy-3-methoxybenzyl alcohol
1.4
5-(hydroxymethyl)furfural
0.21 - 4
5-formylfuran-2-carboxylate
1.6
5-hydroxymethylfurfural
pH 6.0, 25C
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
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 0.011
(S)-1-phenylethanol
31.4
2,5-diformylfuran
pH 6.0, 25C
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8.6
4-(Hydroxymethyl)benzaldehyde
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pH 7.0, 25C
0.0047 - 21
4-Hydroxy-3-methoxybenzyl alcohol
9.9
5-(hydroxymethyl)furfural
0.056 - 0.46
5-formylfuran-2-carboxylate
20.1
5-hydroxymethylfurfural
pH 6.0, 25C
1.6
furan-2,5-dicarbaldehyde
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pH 7.0, 25C
1.3
terephthaldehyde
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pH 7.0, 25C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0001 - 0.00055
(S)-1-phenylethanol
0.157
2,5-diformylfuran
pH 6.0, 25C
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0.0167
2,5-hydroxymethylfurancarboxylic acid
pH 6.0, 25C
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57
4-(Hydroxymethyl)benzaldehyde
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pH 7.0, 25C
0.0057 - 29
4-Hydroxy-3-methoxybenzyl alcohol
7 - 7.1
5-(hydroxymethyl)furfural
0.005 - 2.2
5-formylfuran-2-carboxylate
0.215
5-hydroxymethylfurfural
pH 6.0, 25C
0.94
furan-2,5-dicarbaldehyde
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pH 7.0, 25C
15
terephthaldehyde
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pH 7.0, 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Methylovorus sp. (strain MP688)
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
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 16-22% (w/v) PEG3350 and 200 mM magnesium formate
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
HisTrap column chromatography and Superdex 200 gel filtration
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recombinant enzyme from Escherichia coli
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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expression in Escherichia coli
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gene aao, recombinant enzyme expression in Escherichia coli
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
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
5-hydroxymethylfurfural increases the expression, translation, and activity of enzymes involved in the ligninolytic system, including aryl-alcohol oxidases and a dehydrogenase
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F434A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
M103A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
N511A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
V367
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the mutant shows increased activity with 5-formylfuran-2-carboxylate compared to the wild type enzyme
V367K
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
V367R/W466F
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the mutant shows strongly increased activity with 5-formylfuran-2-carboxylate compared to the wild type enzyme
V465A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
W369A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
W466A
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the mutant shows reduced activity with 4-hydroxy-3-methoxybenzyl alcohol compared to the wild type enzyme
W466F
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the mutant shows increased activity with 5-formylfuran-2-carboxylate compared to the wild type enzyme
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biofuel production
synthesis
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biocatalytic production of furan-2,5-dicarboxylate, a biobased platform chemical for the production of polymers