Tunable Production of (R)- or (S)-Citronellal from Geraniol via a Bienzymatic Cascade Using a Copper Radical Alcohol Oxidase and Old Yellow Enzyme
David Ribeaucourt (Aix Marseille Université)
G.T. Höfler (TU Delft - BT/Biocatalysis)
Mehdi Yemloul (Aix Marseille Université)
Bastien Bissaro (Aix Marseille Université)
Fanny Lambert (V. Mane Fils)
Jean Guy Berrin (Aix Marseille Université)
Mickael Lafond (Aix Marseille Université)
C.E. Paul (TU Delft - BT/Biocatalysis)
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Abstract
Biocatalytic pathways for the synthesis of (-)-menthol, the most sold flavor worldwide, are highly sought-after. To access the key intermediate (R)-citronellal used in current major industrial production routes, we established a one-pot bienzymatic cascade from inexpensive geraniol, overcoming the problematic biocatalytic reduction of the mixture of (E/Z)-isomers in citral by harnessing a copper radical oxidase (CgrAlcOx) and an old yellow enzyme (OYE). The cascade using OYE2 delivered 95.1% conversion to (R)-citronellal with 95.9% ee, a 62 mg scale-up affording high yield and similar optical purity. An alternative OYE, GluER, gave (S)-citronellal from geraniol with 95.3% conversion and 99.2% ee.
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