1.1.3.47: 5-(hydroxymethyl)furfural oxidase
This is an abbreviated version!
For detailed information about 5-(hydroxymethyl)furfural oxidase, go to the full flat file.
Word Map on EC 1.1.3.47
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1.1.3.47
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synthesis
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2,5-furandicarboxylic
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biocatalyst
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bio-based
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biocatalytic
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oxidases
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putida
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methylovorus
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basilensis
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fed-batch
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petroleum-based
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terephthalate
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cupriavidus
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flavin
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ornithinolytica
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biomass-derived
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raoultella
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eugenol
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enantioselective
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polyesters
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cosolvents
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one-pot
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fusing
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biotechnology
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biofuel production
- 1.1.3.47
- synthesis
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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
Reaction
Synonyms
5-hydroxymethylfurfural oxidase, AAO, AOX1, GaoB, Glox2, Glox3, GLRG_02805, HFMO, HMF oxidase, HMF/furfural oxidoreductase, HmfH, HMFO, MPQ_0130
ECTree
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Substrates Products
Substrates Products on EC 1.1.3.47 - 5-(hydroxymethyl)furfural oxidase
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REACTION DIAGRAM
(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
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?
(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
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?
(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
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?
(2R,3E)-4-phenylbut-3-en-2-ol + O2
(3E)-4-phenylbut-3-en-2-one + H2O2
29% conversion, 25% enantiomeric excess
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?
(2R,3E)-oct-3-en-2-ol + O2
(3E)-oct-3-en-2-one + H2O2
16% conversion, 19% enantiomeric excess
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?
1-(4-chlorophenyl)ethanethiol + O2
1-(4-chlorophenyl)ethane-1-thione + (R)-1-(4-chlorophenyl)ethanethiol
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?
1-(4-fluorophenyl)ethanethiol + O2
1-(4-fluorophenyl)ethane-1-thione + (R)-1-(4-fluorophenyl)ethanethiol
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?
1-(4-methylphenyl)ethanethiol + O2
1-(4-methylphenyl)ethane-1-thione + (R)-1-(4-methylphenyl)ethanethiol
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?
1-phenylethanethiol + O2
1-phenylethane-1-thione + (R)-1-phenylethanethiol
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?
2,5-diformylfuran + O2
formylfurancarboxylic acid + ?
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?
2,5-hydroxymethylfurancarboxylic acid + O2
2,5-furandicarboxylic acid + H2O2
very low activity
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?
4-hydroxy-3-methoxybenzyl alcohol + O2
4-hydroxy-3-methoxybenzaldehyde + H2O2
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?
4-methoxybenzyl alcohol + O2
4-methoxybenzyl aldehyde + H2O2
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?
5-(hydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
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?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
2,5-formylfurancarboxylic acid + H2O2
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?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
2,5-furandicarboxylic acid + ?
very low activity
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?
5-(hydroxymethyl)furan-2-carboxylic acid + O2
furan-2-carbaldehyde-5-carboxylate + H2O2
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?
5-(hydroxymethyl)furfural + O2
5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
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?
5-formylfuran-2-carboxylate + H2O
5-(dihydroxymethyl)furan-2-carboxylate
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?
5-hydroxymethylfurfural + O2
5-hydroxymethylfuran-2-carboxylic acid + H2O2
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?
formylfurancarboxylic acid + O2
2,5-furandicarboxylic acid + H2O2
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?
furan-2,5-dicarbaldehyde + H2O
5-(dihydroxymethyl)furan-2-carbaldehyde
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?
furan-2,5-dicarbaldehyde + O2
furan-2-carbaldehyde-5-carboxylate + H2O2
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?
furan-2-carbaldehyde-5-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
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?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
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?
2,5-diformylfuran + 2 O2
2,5-furandicarboxylic acid + H2O2
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?
5-formylfuran-2-carboxylic acid + ?
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?
2,5-diformylfuran + O2
5-formylfuran-2-carboxylic acid + ?
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?
3-methoxybenzaldehyde + H2O2
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?
3-methoxybenzyl alcohol + O2
3-methoxybenzaldehyde + H2O2
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?
4-methoxybenzaldehyde + H2O2
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?
4-methoxybenzyl alcohol + O2
4-methoxybenzaldehyde + H2O2
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?
5-formylfuran-2-carboxylate + H2O2
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?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
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spontaneous formation of 5-(dihydroxymethyl)furan-2-carboxylate from 5-formylfuran-2-carboxylate
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?
5-(dihydroxymethyl)furan-2-carbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
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spontaneous formation of 5-(dihydroxymethyl)furan-2-carboxylate from 5-formylfuran-2-carboxylate
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?
furan-2,5-dicarboxylate + H2O2
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?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
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?
5-(dihydroxymethyl)furan-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
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?
furan-2,5-dicarboxylic acid + ?
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5-(hydroxymethyl)furan-2-carboxylic acid + O2
furan-2,5-dicarboxylic acid + ?
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furan-2,5-dicarboxylate + 3 H2O2
overall reaction
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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
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5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
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?
5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
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overall reaction
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5-(hydroxymethyl)furfural + 3 O2 + 2 H2O
furan-2,5-dicarboxylate + 3 H2O2
overall reaction
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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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furan-2,5-dicarbaldehyde + H2O2
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5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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spontaneous formation of 5-(dihydroxymethyl)furan-2-carbaldehyde from furan-2,5-dicarbaldehyde
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?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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spontaneous formation of 5-(dihydroxymethyl)furan-2-carbaldehyde from furan-2,5-dicarbaldehyde
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?
5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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5-(hydroxymethyl)furfural + O2
furan-2,5-dicarbaldehyde + H2O2
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?
furan-2,5-dicarboxylate + H2O2
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?
5-formylfuran-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
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?
5-formylfuran-2-carboxylate + O2
furan-2,5-dicarboxylate + H2O2
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?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
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?
5-hydroxymethylfurfural + O2
2,5-diformylfuran + H2O2
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?
2,5-furandicarboxylic acid + ?
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5-hydroxymethylfurfural + O2
2,5-furandicarboxylic acid + ?
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5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
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5-hydroxymethylfurfural + O2
5-(hydroxymethyl)furan-2-carboxylic acid + H2O2
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cinnamyl alcohol + O2
cinnamaldehyde + H2O2
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5-formylfuran-2-carboxylate + H2O2
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?
furan-2,5-dicarbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
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?
furan-2,5-dicarbaldehyde + O2
5-formylfuran-2-carboxylate + H2O2
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veratryl alcohol + O2
veratryl aldehyde + H2O2
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?
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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
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additional information
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enzyme displays weak activity on carbohydrates
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additional information
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enzyme displays weak activity on carbohydrates
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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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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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additional information
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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
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additional information
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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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additional information
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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
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additional information
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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
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additional information
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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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additional information
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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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