Scent of a Strawberry

Scent of a Strawberry

Author: Melania Tesio

Fresh strawberries owe their typical aroma to the volatile compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, pictured). During ripening, the NAD(P)H dependent enzyme Fragaria x ananassa enone oxidoreductase (FaEO) synthesizes HDMF by reducing an exocyclic double bond present in 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone (HMMF).

The exact mechanisms of this reaction have been elucidated by André Schiefner and colleagues, Technische Universität München, Germany. The scientists revealed that FaEO transfers a hydride ion from NAD(P)H to HMMF’s unsaturated exocyclic C6 carbon. In doing so, FaEO generates a cyclic non-chiral enolate intermediate which is converted into HDMF following protonation. By elucidating the structural basis that regulates HDMF synthesis, this study offers new insights to improve the production of a volatile largely used in the food and perfume industries.

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