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Information on EC 1.3.1.105 - 2-methylene-furan-3-one reductase
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EC Tree
1.3.1.105 2-methylene-furan-3-one reductaseIUBMB 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.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
2-methylene-furan-3-one reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FaEO
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxy-2,5-dimethylfuran-3(2H)-one + NADP+ = 4-hydroxy-5-methyl-2-methylenefuran-3(2H)-one + NADPH + H+
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
,
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SYSTEMATIC NAME
IUBMB Comments
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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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
(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+
-
-
-
?
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
-
-
?
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
-
-
?
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADPH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NADP+
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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)-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)-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 + NADH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
-
-
-
-
?
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 + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
-
-
-
-
?
additional information
?
-
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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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
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
preferred cofactor, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
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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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Zn2+
Zn2+
-
presence of putative Zn2+ binding regions localized in the opposite side with respect to the calmodulin binding region
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.012
9,10-phenanthrenequinone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
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
-
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
-
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
1.59
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
-
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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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.15
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
-
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
-
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
-
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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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
650
9,10-phenanthrenequinone
0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
0.14
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
-
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
-
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
-
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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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). 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)
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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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
solubilization from membrane using n-dodecyl-beta-D-maltoside or n-octyl-beta-D-glucopyranoside
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli K-12
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
protein may be expressed in different isoforms by alternative gene splicing
-
the enzyme is up-accumulated in plants colonized with the arbuscular mycorrhizal fungus Rhizophagus irregularis
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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)
-
brenda
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