Tunable Production of ( R )- or ( S )-Citronellal from Geraniol via a Bienzymatic Cascade Using a Copper Radical Alcohol Oxidase and Old Yellow Enzyme - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Access content directly
Journal Articles ACS Catalysis Year : 2022

Tunable Production of ( R )- or ( S )-Citronellal from Geraniol via a Bienzymatic Cascade Using a Copper Radical Alcohol Oxidase and Old Yellow Enzyme

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% cc, a 62 mg scaleup affording high yield and similar optical purity. An alternative OYE, GIuER, gave (S)-citronellal from geraniol with 95.3% conversion and 99.2% ee.

Dates and versions

hal-03582992 , version 1 (21-02-2022)

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David Ribeaucourt, Georg Höfler, Mehdi Yemloul, Bastien Bissaro, Fanny Lambert, et al.. Tunable Production of ( R )- or ( S )-Citronellal from Geraniol via a Bienzymatic Cascade Using a Copper Radical Alcohol Oxidase and Old Yellow Enzyme. ACS Catalysis, 2022, 12 (2), pp.1111-1116. ⟨10.1021/acscatal.1c05334⟩. ⟨hal-03582992⟩
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