Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 6, Pages 1049-1057Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201601064
Keywords
Deep Eutectic Solvents; Green chemistry; Whole-cell catalysis; Ketones; Reduction; Alcohols
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Funding
- University of Bari within the framework of the Project Sviluppo di nuove metodologie di sintesi mediante l'impiego di biocatalizzatori e solventi a basso impatto ambientale [Perna01333214Ricat]
- Interuniversities Consortium C.I.N.M.P.I.S
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In this contribution, we report the first successful baker's yeast reduction of arylpropanones using deep eutectic solvents (DESs) as biodegradable and non-hazardous co-solvents. The nature of DES [e.g. choline chloride/glycerol (2: 1)] and the percentage of water in the mixture proved to be critical for both the reversal of selectivity and to achieve high enantioselectivity on going from pure water (up to 98: 2 er in favour of the Senantiomer) to DES/aqueous mixtures (up to 98: 2 er in favour of the R-enantiomer). As a result, both enantiomers of valuable chiral alcohols of pharmaceutical interest were prepared from the same biocatalyst by simply switching the solvent. The possible inhibition of some (S)-oxidoreductases making part of the genome of such a wild-type whole cell biocatalyst when DESs are used as cosolvents may pave the way for an anti-Prelog reduction. The scope and limitations of this kind of biotransformations for a range of aryl-containing ketones are also discussed.
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