Enantioselective synthesis of (R)-citronellal from geraniol with an immobilised copper alcohol oxidase and ene reductase.

IF 3.4 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Beatrice Tagliabue, Christian M Heckmann, Rocio Villa, Sacha Grisel, Jean-Guy Berrin, Mickael Lafond, David Ribeaucourt, Caroline E Paul
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引用次数: 0

Abstract

(R)-Citronellal is one of the key chiral intermediates in the synthesis of the isomer (-)-menthol, one of the most commercialised terpenoid flavours worldwide. Enzymatic approaches could represent a less energy-demanding alternative for its synthesis, such as a previously reported bienzymatic cascade starting from inexpensive, commercially available geraniol. A copper radical oxidase (CgrAlcOx) followed by a flavin-dependent ene reductase (OYE2) were used to obtain (R)-citronellal. Here, we used a metal-affinity immobilisation strategy on the His-tagged enzymes for the cascade and studied enzyme recovery and reusability as well as increased solvent tolerance. After screening a panel of resins for enzyme immobilisation and water-immiscible co-solvents, we successfully obtained 95% conversion to (R)-citronellal with 96.9% enantiomeric excess (ee) in a concurrent cascade after 7 h of reaction time, starting from 10 mM of geraniol.

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来源期刊
Reaction Chemistry & Engineering
Reaction Chemistry & Engineering Chemistry-Chemistry (miscellaneous)
CiteScore
6.60
自引率
7.70%
发文量
227
期刊介绍: Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society. From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.
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