Any feedback?
Please rate this page
(enzyme.php)
(0/150)

BRENDA support

BRENDA Home
show all | hide all No of entries

Information on EC 1.3.1.105 - 2-methylene-furan-3-one reductase and Organism(s) Fragaria vesca and UniProt Accession O23939

for references in articles please use BRENDA:EC1.3.1.105
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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.
Specify your search results
Select one or more organisms in this record: ?
This record set is specific for:
Fragaria vesca
UNIPROT: O23939
Show additional data
Do not include text mining results
Include (text mining) results
Include results (AMENDA + additional results, but less precise)
The taxonomic range for the selected organisms is: Fragaria vesca
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
2-methylene-furan-3-one reductase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PATHWAY SOURCE
PATHWAYS
-
-, -
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.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(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
-
-
-
?
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
-
-
?
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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
0.361
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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
ENOX_FRAVE
322
0
34174
Swiss-Prot
other Location (Reliability: 3)
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
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli K-12
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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)
Manually annotated by BRENDA team