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

Autor: David Ribeaucourt, Georg T. Höfler, Mehdi Yemloul, Bastien Bissaro, Fanny Lambert, Jean-Guy Berrin, Mickael Lafond, Caroline E. Paul
Přispěvatelé: Biodiversité et Biotechnologie Fongiques (BBF), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Catalysis Engineering - ChemE, Delft University of Technology, Van der Maasweg 9, 2629HZ Delft, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), V MANE Fils, NWO Open Competition Science - XSOCENW.XS4.291, ANR-17-CE07-0047,FUNTASTIC,Nouvelles oxydases à radical cuivre fongiques utilisées comme biocatalyseurs pour la valorisation de la biomasse végétale et d'alcools(2017)
Rok vydání: 2022
Předmět:
Zdroj: ACS Catalysis
ACS Catalysis, 2022, 12 (2), pp.1111-1116. ⟨10.1021/acscatal.1c05334⟩
ACS Catalysis, 12(2)
ISSN: 2155-5435
DOI: 10.1021/acscatal.1c05334
Popis: International audience; 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.
Databáze: OpenAIRE
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