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EC Tree
IUBMB Comments The enzyme was dicovered in strawberry (Fragaria x ananassa), where it produces furaneol, one of the major aroma compounds in the fruits. It has also been detected in tomato (Solanum lycopersicum) and pineapple (Ananas comosus). The enzyme can also act on derivatives substituted at the methylene functional group. The enzyme from the yeast Saccharomyces cerevisiae acts on (2E)-2-ethylidene-4-hydroxy-5-methylfuran-3(2H)-one and produces homofuraneol, an important aroma compound in soy sauce and miso. NADPH is the preferred cofactor.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
2-methylene-furan-3-one reductase,
more
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FaEO
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4-hydroxy-2,5-dimethylfuran-3(2H)-one + NADP+ = 4-hydroxy-5-methyl-2-methylenefuran-3(2H)-one + NADPH + H+
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4-hydroxy-2,5-dimethylfuran-3(2H)-one:NAD(P)+ oxidoreductase
The enzyme was dicovered in strawberry (Fragaria x ananassa), where it produces furaneol, one of the major aroma compounds in the fruits. It has also been detected in tomato (Solanum lycopersicum) and pineapple (Ananas comosus). The enzyme can also act on derivatives substituted at the methylene functional group. The enzyme from the yeast Saccharomyces cerevisiae acts on (2E)-2-ethylidene-4-hydroxy-5-methylfuran-3(2H)-one and produces homofuraneol, an important aroma compound in soy sauce and miso. NADPH is the preferred cofactor.
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(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-butyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone + NADH + H+
4-hydroxy-5-methyl-2-propyl-3(2H)-furanone + NAD+
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADPH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone + NADP+
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?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
(2R)-4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
kcat/Km for NADH is 7.5fold lower than for NADPH, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
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?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADPH + H+
(2R)-4-hydroxy-2,5-dimethyl-3(2H)-furanone + NADP+
kcat/Km for NADH is 7.5fold lower than for NADPH, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
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?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADPH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NADP+
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9,10-phenanthrenequinone + NADH + H+
? + NAD+
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?
additional information
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(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-butyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
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?
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-butyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
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?
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone + NADH + H+
4-hydroxy-5-methyl-2-propyl-3(2H)-furanone + NAD+
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?
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone + NADH + H+
4-hydroxy-5-methyl-2-propyl-3(2H)-furanone + NAD+
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?
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
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?
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
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?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
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?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
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additional information
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no reaction with (2E)-2-hexenal, (3E)-3-hexen-2-one, (3E)-5-methyl-3-hexen-2-one, cyclohexa-1,2-dione, buta-2,3-dione, coumarin, astaxanthin, cinnamyl aldehyde, 4-coumaric acid, ferulic acid, dimethoxycinnamic acid, or benzil
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additional information
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no reaction with (2E)-2-hexenal, (3E)-3-hexen-2-one, (3E)-5-methyl-3-hexen-2-one, cyclohexa-1,2-dione, buta-2,3-dione, coumarin, astaxanthin, cinnamyl aldehyde, 4-coumaric acid, ferulic acid, dimethoxycinnamic acid, or benzil
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?
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4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
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FAD
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cofactor occurs in a mix of both oxidation states
NADPH
preferred cofactor, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
NADH
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NADH
kcat/Km for NADH is 7.5fold lower than for NADPH, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
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Zn2+
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Zn2+
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presence of putative Zn2+ binding regions localized in the opposite side with respect to the calmodulin binding region
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EDTA
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presence of EDTA induces monomerization
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0.82 - 1.13
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
1.04 - 2.41
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
1.59 - 2.14
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.012
9,10-phenanthrenequinone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.361
NADH
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
0.325
NADPH
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
0.82
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.13
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.04
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
2.41
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.59
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
2.14
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
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0.15 - 1.43
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.34 - 2.69
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
0.39 - 1.94
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.15
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.43
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.34
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
2.69
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.39
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.94
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
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0.14 - 1.9
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.14 - 2.6
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
0.25 - 0.9
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
650
9,10-phenanthrenequinone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
20
NADH
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
150
NADPH
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
0.14
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.9
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.14
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
2.6
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.25
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.9
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
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UniProt
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UniProt
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UniProt
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brenda
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protein contains a calmodulin-binding region
brenda
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metabolism
(2R)-4-hydroxy-2,5-dimethyl-3(2H)-furanone is synthesized during the fruit-ripening process as a major aroma compound (55 mg/kg) of strawberry fruits
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ENOXC_FRAAN
323
0
34296
Swiss-Prot
other Location (Reliability: 3 )
ENOXE_FRAAN
322
0
34226
Swiss-Prot
other Location (Reliability: 3 )
ENOX_FRAVE
322
0
34174
Swiss-Prot
other Location (Reliability: 3 )
ENOX_SOLLC
388
0
41001
Swiss-Prot
Chloroplast (Reliability: 1 )
A0A5B7CEY8_DAVIN
338
0
36918
TrEMBL
other Location (Reliability: 3 )
A0A2P6S5F4_ROSCH
322
0
34161
TrEMBL
other Location (Reliability: 3 )
A0A8J5E6G9_9ASCO
342
0
36895
TrEMBL
other Location (Reliability: 1 )
G7KKH5_MEDTR
309
0
33274
TrEMBL
other Location (Reliability: 2 )
A0A0B8NH87_9NOCA
263
0
26458
TrEMBL
-
A0A5B7AFC3_DAVIN
396
0
41847
TrEMBL
Chloroplast (Reliability: 1 )
A0A8J5EGS1_9ASCO
330
0
35706
TrEMBL
other Location (Reliability: 3 )
A0A8J5BII0_9ASCO
350
0
37969
TrEMBL
other Location (Reliability: 3 )
A0A8J5EIE1_9ASCO
346
0
37403
TrEMBL
other Location (Reliability: 1 )
G7KKH6_MEDTR
320
0
34506
TrEMBL
other Location (Reliability: 2 )
A0A8J5BCM2_9ASCO
284
0
30264
TrEMBL
other Location (Reliability: 1 )
A0A8J5B6B2_9ASCO
349
0
37608
TrEMBL
other Location (Reliability: 2 )
A0A8J5E565_9ASCO
346
0
37462
TrEMBL
other Location (Reliability: 1 )
A0A2P6S5E8_ROSCH
65
0
7209
TrEMBL
other Location (Reliability: 4 )
A0A396HCY0_MEDTR
328
0
35782
TrEMBL
other Location (Reliability: 2 )
A0A396HJT4_MEDTR
81
0
9119
TrEMBL
other Location (Reliability: 2 )
A0A396HJ19_MEDTR
328
0
35770
TrEMBL
other Location (Reliability: 2 )
A0A2P6S5D4_ROSCH
322
0
34184
TrEMBL
other Location (Reliability: 3 )
A0A072TZA9_MEDTR
317
0
33944
TrEMBL
other Location (Reliability: 2 )
A0A2P6S5M6_ROSCH
341
0
36115
TrEMBL
other Location (Reliability: 2 )
A0A5B7ABV5_DAVIN
337
0
36024
TrEMBL
Secretory Pathway (Reliability: 5 )
A0A2P6S5C7_ROSCH
343
0
36458
TrEMBL
other Location (Reliability: 3 )
A0A8J5EMN1_9ASCO
340
0
36590
TrEMBL
other Location (Reliability: 2 )
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34300
x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
37000
x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
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dimer
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2 * 42000, SDS-PAGE
?
x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
?
x * 40400, calculated from amino acid sequence
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crystallisation in complex with NADPH and 4-hydroxy-2,5-dimethyl-3(2H)-furanone or in complex with NADPH and 4-hydroxy-5-methyl-3(2H)-furanone. The crystal structure of FaEO was solved by molecular replacement using a published X-ray structure of a quinone oxidoreductase from Thermus thermophilus. The structure belongs to the zinc-independent medium chain dehydrogenase/reductase family
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gel filtration, anion exchange chromatography
gel filtration, ion exchange chromatography
solubilization from membrane using n-dodecyl-beta-D-maltoside or n-octyl-beta-D-glucopyranoside
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expressed in Escherichia coli K-12
expressed in Escherichia coli K-12
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expressed in Escherichia coli K-12
expressed in Escherichia coli K-12
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protein may be expressed in different isoforms by alternative gene splicing
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the enzyme is up-accumulated in plants colonized with the arbuscular mycorrhizal fungus Rhizophagus irregularis
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Klein, D.; Fink, B.; Arold, B.; Eisenreich, W.; Schwab, W.
Functional characterization of enone oxidoreductases from strawberry and tomato fruit
J. Agric. Food Chem.
55
6705-6711
2007
Solanum lycopersicum, Fragaria x ananassa (Q941I0)
brenda
Schiefner, A.; Sinz, Q.; Neumaier, I.; Schwab, W.; Skerra, A.
Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone
J. Biol. Chem.
288
16815-16826
2013
Fragaria vesca (O23939)
brenda
Raab, T.; Lopez-Raez, J.A.; Klein, D.; Caballero, J.L.; Moyano, E.; Schwab, W.; Munoz-Blanco, J.
FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase
Plant Cell
18
1023-1037
2006
Fragaria x ananassa (Q941I0)
brenda
Collu, G.; Farci, D.; Esposito, F.; Pintus, F.; Kirkpatrick, J.; Piano, D.
New insights into the operative network of FaEO, an enone oxidoreductase from Fragaria x ananassa Duch.
Plant Mol. Biol.
94
125-136
2017
Fragaria x ananassa
brenda
Peinado-Guevara, L.; Lpez-Meyer, M.; Lpez-Valenzuela, J.; Maldonado-Mendoza, I.; Galindo-Flores, H.; Campista-Len, S.; Medina-Godoy, S.
Comparative proteomic analysis of leaf tissue from tomato plants colonized with Rhizophagus irregularis
Symbiosis
73
93-106
2017
Solanum lycopersicum (K4BW79)
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brenda
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