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Information on EC 1.1.3.47 - 5-(hydroxymethyl)furfural oxidase
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EC Tree
1.1.3.47 5-(hydroxymethyl)furfural oxidaseIUBMB Comments
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 . The enzyme has a broad substrate range that overlaps with EC 1.1.3.7, aryl-alcohol oxidase.
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Word Map
- 1.1.3.47
- synthesis
-
2,5-furandicarboxylic
-
biocatalyst
-
bio-based
-
biocatalytic
- oxidases
- putida
- methylovorus
- basilensis
-
fed-batch
-
petroleum-based
- terephthalate
-
cupriavidus
- flavin
- ornithinolytica
-
biomass-derived
-
raoultella
- eugenol
-
enantioselective
-
polyesters
-
cosolvents
-
one-pot
-
fusing
- biotechnology
- biofuel production
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
+
3
+
2
=
+
3
Synonyms
5-hydroxymethylfurfural oxidase, hmf oxidase, hmf/furfural oxidoreductase, 5-(hydroxymethyl)furfural oxidase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AAO
AOX1
GaoB
GLRG_02805
HMFO
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5-(dihydroxymethyl)furan-2-carbaldehyde + O2 = 5-formylfuran-2-carboxylate + H2O2
(1c)
-
-
-
5-(dihydroxymethyl)furan-2-carboxylate + O2 = furan-2,5-dicarboxylate + H2O2
(1e)
-
-
-
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O = furan-2,5-dicarboxylate + 3 H2O2
overall reaction
-
-
-
5-(hydroxymethyl)furfural + O2 = furan-2,5-dicarbaldehyde + H2O2
(1a)
-
-
-
5-formylfuran-2-carboxylate + H2O = 5-(dihydroxymethyl)furan-2-carboxylate
(1d), spontaneous
-
-
-
furan-2,5-dicarbaldehyde + H2O = 5-(dihydroxymethyl)furan-2-carbaldehyde
(1b), spontaneous
-
-
-
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PATHWAY SOURCE
PATHWAYS
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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.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2R,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol + O2
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + H2O2
4% conversion, 2% enantiomeric excess
-
-
?
(2R,3E)-4-(4-chlorophenyl)but-3-en-2-ol + O2
(3E)-4-(4-chlorophenyl)but-3-en-2-one + H2O2
10% conversion, 10% enantiomeric excess
-
-
?
(2R,3E)-4-(4-methylphenyl)but-3-en-2-ol + O2
(3E)-4-(4-methylphenyl)but-3-en-2-one + H2O2
13% conversion, 14% enantiomeric excess
-
-
?
(2R,3E)-4-phenylbut-3-en-2-ol + O2
(3E)-4-phenylbut-3-en-2-one + H2O2
29% conversion, 25% enantiomeric excess
-
-
?
(2R,3E)-oct-3-en-2-ol + O2
(3E)-oct-3-en-2-one + H2O2
16% conversion, 19% enantiomeric excess
-
-
?
1-(4-chlorophenyl)ethanethiol + O2
1-(4-chlorophenyl)ethane-1-thione + (R)-1-(4-chlorophenyl)ethanethiol
-
-
-
?
1-(4-fluorophenyl)ethanethiol + O2
1-(4-fluorophenyl)ethane-1-thione + (R)-1-(4-fluorophenyl)ethanethiol
-
-
-
?
1-(4-methylphenyl)ethanethiol + O2
1-(4-methylphenyl)ethane-1-thione + (R)-1-(4-methylphenyl)ethanethiol
-
-
-
?
1-phenylethanethiol + O2
1-phenylethane-1-thione + (R)-1-phenylethanethiol
-
-
-
?
2,5-diformylfuran + O2
formylfurancarboxylic acid + ?
-
-
-
?
2,5-hydroxymethylfurancarboxylic acid + O2
2,5-furandicarboxylic acid + H2O2
very low activity
-
-
?
4-hydroxy-3-methoxybenzyl alcohol + O2
4-hydroxy-3-methoxybenzaldehyde + H2O2
-
-
-
?
4-methoxybenzyl alcohol + O2
4-methoxybenzyl aldehyde + H2O2
-
-
-
?
5-(hydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
2,5-formylfurancarboxylic acid + H2O2
-
-
-
?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
2,5-furandicarboxylic acid + ?
very low activity
-
-
?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
furan-2-carbaldehyde-5-carboxylate + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + O2
5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
-
-
-
?
5-formylfuran-2-carboxylate + H2O
5-(dihydroxymethyl)furan-2-carboxylate
-
-
-
?
5-hydroxymethylfurfural + O2
5-hydroxymethylfuran-2-carboxylic acid + H2O2
-
-
-
?
formylfurancarboxylic acid + O2
2,5-furandicarboxylic acid + H2O2
-
-
-
?
furan-2,5-dicarbaldehyde + H2O
5-(dihydroxymethyl)furan-2-carbaldehyde
-
-
-
?
furan-2,5-dicarbaldehyde + O2
furan-2-carbaldehyde-5-carboxylate + H2O2
-
-
-
?
furan-2-carbaldehyde-5-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
-
-
-
?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
-
-
-
?
2,5-diformylfuran + O2
5-formylfuran-2-carboxylic acid + ?
-
-
-
?
2,5-diformylfuran + O2
5-formylfuran-2-carboxylic acid + ?
-
-
-
?
3-methoxybenzyl alcohol + O2
3-methoxybenzaldehyde + H2O2
-
-
-
?
3-methoxybenzyl alcohol + O2
3-methoxybenzaldehyde + H2O2
-
-
-
?
4-methoxybenzyl alcohol + O2
4-methoxybenzaldehyde + H2O2
-
-
-
?
4-methoxybenzyl alcohol + O2
4-methoxybenzaldehyde + H2O2
-
-
-
?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
spontaneous formation of 5-(dihydroxymethyl)furan-2-carboxylate from 5-formylfuran-2-carboxylate
-
?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
spontaneous formation of 5-(dihydroxymethyl)furan-2-carboxylate from 5-formylfuran-2-carboxylate
-
?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
-
?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
furan-2,5-dicarboxylic acid + ?
-
-
-
?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
furan-2,5-dicarboxylic acid + ?
-
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction. the enzyme is involved in degradation of 5-(hydroxymethyl)furfural
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
-
overall reaction
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
the enzyme is involved in the degradation and detoxification of 5-(hydroxymethyl)furfural
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
spontaneous formation of 5-(dihydroxymethyl)furan-2-carbaldehyde from furan-2,5-dicarbaldehyde
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
spontaneous formation of 5-(dihydroxymethyl)furan-2-carbaldehyde from furan-2,5-dicarbaldehyde
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
?
5-formylfuran-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
?
5-formylfuran-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
-
?
5-formylfuran-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-furandicarboxylic acid + ?
-
-
-
?
5-hydroxymethylfurfural + O2
2,5-furandicarboxylic acid + ?
-
-
-
?
5-hydroxymethylfurfural + O2
5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
-
-
-
?
5-hydroxymethylfurfural + O2
5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
-
-
-
?
cinnamyl alcohol + O2
cinnamaldehyde + H2O2
-
-
-
?
furan-2,5-dicarbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
?
furan-2,5-dicarbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
-
?
furan-2,5-dicarbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
-
?
veratryl alcohol + O2
veratryl aldehyde + H2O2
-
-
-
?
additional information
?
-
enzyme is active on short-chain alkane diols and glycerol, and aryl alcohols, with similar specific activity values. Highest specific activity is observed on 5-hydroxymethylfurfural. Galactose and galactosylated oligosaccharides are poor substrates
-
-
-
additional information
?
-
enzyme displays weak activity on carbohydrates
-
-
-
additional information
?
-
enzyme displays weak activity on carbohydrates
-
-
-
additional information
?
-
the enzyme has a broad substrate range that overlaps with EC 1.1.3.7, aryl-alcohol oxidase
-
-
?
additional information
?
-
-
the enzyme has a broad substrate range that overlaps with EC 1.1.3.7, aryl-alcohol oxidase
-
-
?
additional information
?
-
for sec-allylic alcohol substrates, exclusively oxidation of the allylic alcohol to the alpha,beta-unsaturated ketone is observed. The reaction is enantioselective for the R-enantiomer
-
-
-
additional information
?
-
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
-
-
?
additional information
?
-
enzyme AAO is also able to oxidize some furanic compounds such as 5-hydroxymethylfurfural (HMF) and 2,5-diformylfuran (DFF), it has very low activity on 2,5-hydroxymethylfurancarboxylic acid, no activity with 2,5-formylfurancarboxylic acid. NMR analysis of the compounds
-
-
?
additional information
?
-
for complete oxidation of 5-hydroxymethylfurfural, the rate-limiting step lies in the final oxidation of the intermediate 5-formyl-furancarboxylic acid to 2,5-furandicarboxylic acid. Wild-type AAO is not able to catalyze 5-formyl-furancarboxylic acid oxidation
-
-
-
additional information
?
-
major reaction product of the cascade is furan-2-carbaldehyde-5-carboxylate. The oxidation of 5-(hydroxymethyl)furfural is significantly boosted in the presence of catalase, leading to 70% yield
-
-
-
additional information
?
-
major reaction product of the cascade is furan-2-carbaldehyde-5-carboxylate. The oxidation of 5-(hydroxymethyl)furfural is significantly boosted in the presence of catalase, leading to 70% yield
-
-
-
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
-
-
-
?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
-
-
-
?
5-formylfuran-2-carboxylate + H2O
5-(dihydroxymethyl)furan-2-carboxylate
-
-
-
?
furan-2,5-dicarbaldehyde + H2O
5-(dihydroxymethyl)furan-2-carbaldehyde
-
-
-
?
additional information
?
-
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
-
-
?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
-
-
-
?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
-
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction. the enzyme is involved in degradation of 5-(hydroxymethyl)furfural
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
-
-
?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
the enzyme is involved in the degradation and detoxification of 5-(hydroxymethyl)furfural
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
H2O2
inhibitory to the oxidation of formylfurancarboxylic acid, oxidation activities of AAO on 5-hydroxymethylfurfural and 2,5-diformylfuran are independent of the presence of H2O2
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.2
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme W466F, at pH 7.5 and 25°C
0.28
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme V367R, at pH 7.5 and 25°C
0.29
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme V367K, at pH 7.5 and 25°C
0.72
4-Hydroxy-3-methoxybenzyl alcohol
wild type enzyme, at pH 7.5 and 25°C
0.82
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme H467A, at pH 7.5 and 25°C
0.92
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme V465A, at pH 7.5 and 25°C
1
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme W466A, at pH 7.5 and 25°C
1.1
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme W369A, at pH 7.5 and 25°C
1.2
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme F434A, at pH 7.5 and 25°C
1.8
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme M103A, at pH 7.5 and 25°C
2
4-Hydroxy-3-methoxybenzyl alcohol
mutant enzyme N511A, at pH 7.5 and 25°C
0.028
4-methoxybenzyl alcohol
pH 6, 25°C, presence of 6 mM formylfurancarboxylic acid
0.038
4-methoxybenzyl alcohol
pH 6, 25°C, presence of 0.8 mM formylfurancarboxylic acid
3.1
5-(hydroxymethyl)furan-2-carboxylic acid
pH 7.5, 25°C
26.9
5-(hydroxymethyl)furan-2-carboxylic acid
wild-type, pH 7,25°C
27
5-(hydroxymethyl)furan-2-carboxylic acid
mutant Y334F, pH 7,25°C
42
5-(hydroxymethyl)furan-2-carboxylic acid
mutant Y334W, pH 7,25°C
0.63
5-(hydroxymethyl)furfural
mutant I73V/H74Y/G356H/V367L/T414K/A419Y/A435E, pH 8.0, 25°C
0.61
5-formyl-2-furan carboxylic acid
pH 6, 30°C
-
0.21
5-formylfuran-2-carboxylate
mutant enzyme V367R/W466F, at pH 7.5 and 25°C
1.4
5-formylfuran-2-carboxylate
mutant enzyme V367R, at pH 7.5 and 25°C
3
5-formylfuran-2-carboxylate
mutant enzyme W466F, at pH 7.5 and 25°C
4
5-formylfuran-2-carboxylate
Km above 4.0 mM, wild type enzyme, at pH 7.5 and 25°C
17
5-hydroxymethylfurfural
</