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, Georg T. Höfler, Mehdi Yemloul, Bastien Bissaro, Fanny Lambert, Jean Guy Berrin, Mickael Lafond*, Caroline E. Paul

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

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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.

Original languageEnglish
Pages (from-to)1111-1116
JournalACS Catalysis
Volume12
Issue number2
DOIs
Publication statusPublished - 2022

Keywords

  • biocascade
  • biocatalysis
  • citral
  • citronellal
  • enzymatic oxidation
  • enzymatic reduction
  • geranial

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