ExplorEnz: EC 1.3.1.105

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1.3.1.105

Accepted name:

2-methylene-furan-3-one reductase

Reaction:

4-hydroxy-2,5-dimethylfuran-3(2H)-one + NADP⁺ = 4-hydroxy-5-methyl-2-methylenefuran-3(2H)-one + NADPH + H⁺

Glossary:

furaneol = 4-hydroxy-2,5-dimethylfuran-3(2H)-one
homofuraneol = 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one

Other name(s):

FaEO; SIEO; enone oxidoreductase; 4-hydroxy-2,5-dimethylfuran-3(2H)-one:NAD(P)⁺ oxidoreductase

Systematic name:

4-hydroxy-2,5-dimethylfuran-3(2H)-one:NADP⁺ oxidoreductase

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.

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc, PDB

References:

1.	Raab, T., Lopez-Raez, J.A., Klein, D., Caballero, J.L., Moyano, E., Schwab, W. and 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 (2006) 1023–1037. [DOI] [PMID: 16517758]
2.	Klein, D., Fink, B., Arold, B., Eisenreich, W. and Schwab, W. Functional characterization of enone oxidoreductases from strawberry and tomato fruit. J. Agric. Food Chem. 55 (2007) 6705–6711. [DOI] [PMID: 17636940]
3.	Schiefner, A., Sinz, Q., Neumaier, I., Schwab, W. and 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 (2013) 16815–16826. [DOI] [PMID: 23589283]
4.	Uehara, K., Watanabe, J., Mogi, Y. and Tsukioka, Y. Identification and characterization of an enzyme involved in the biosynthesis of the 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone in yeast. J. Biosci. Bioeng. 123 (2017) 333–341. [DOI] [PMID: 27865643]

[EC 1.3.1.105 created 2013]