Information on EC 1.3.1.105 - 2-methylene-furan-3-one reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.1.105
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RECOMMENDED NAME
GeneOntology No.
2-methylene-furan-3-one reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-hydroxy-2,5-dimethylfuran-3(2H)-one + NAD(P)+ = 4-hydroxy-5-methyl-2-methylenefuran-3(2H)-one + NAD(P)H + H+
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
furaneol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxy-2,5-dimethylfuran-3(2H)-one:NAD(P)+ oxidoreductase
In the fruit-ripening process of strawberry (Fragaria x ananassa) the reaction is catalysed in the reverse direction from that shown. 4-hydroxy-2,5-dimethylfuran-3(2H)-one is one of the major aroma compounds in the fruits. The enzyme has also been detected in tomato (Solanum lycopersicum) fruits [2]. NADPH is the preferred cofactor.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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+
show the reaction diagram
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone + NADH + H+
4-hydroxy-5-methyl-2-propyl-3(2H)-furanone + NAD+
show the reaction diagram
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone + NADH + H+
2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone + NAD+
show the reaction diagram
(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+
show the reaction diagram
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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+
show the reaction diagram
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+
show the reaction diagram
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADPH + H+
(2R)-4-hydroxy-2,5-dimethyl-3(2H)-furanone + NADP+
show the reaction diagram
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+
show the reaction diagram
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?
9,10-phenanthrenequinone + NADH + H+
? + NAD+
show the reaction diagram
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?
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
4-hydroxy-5-methyl-2-methylene-3(2H)-furanone + NADH + H+
4-hydroxy-2,5-dimethyl-3(2H)-furanone + NAD+
show the reaction diagram
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
preferred cofactor, Re-specific, i.e. the 4R-hydride of NAD(P)H is transferred
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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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
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.14 - 1.9
(2E)-2-butylidene-4-hydroxy-5-methyl-3(2H)-furanone
19730
0.14 - 2.6
(2E)-4-hydroxy-5-methyl-2-propylidene-3(2H)-furanone
19729
0.25 - 0.9
(2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone
14949
650
9,10-phenanthrenequinone
Fragaria x ananassa
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0.1 M Na2HPO4/NaH2PO4, pH 7, 30°C, cofactor NADH
558
20
NADH
Fragaria vesca
O23939
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
8
150
NADPH
Fragaria vesca
O23939
0.1 M K2HPO4/KH2PO4, pH 5.0 or 7.0, 30°C
5
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34300
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x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
37000
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x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 37000, SDS-PAGE, x * 34300, calculation from amino acid sequence
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
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gel filtration, anion exchange chromatography
gel filtration, ion exchange chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli K-12