Plant-mediated stereoselective biotransformations in natural deep eutectic solvents

• DOI: 10.1016/j.procbio.2017.12.010
• Publication Date: 2017-12-29T12:47:39Z
• Authors: Manuela Panić; Maja Majerić Elenkov; Marin Roje; Marina Cvjetko Bu...; Ivana Radojčić Re...
• Keywords: Biocatalysis; Biotransformation; Enantiomeric excess; Biocompatibility; Environmentally Friendly

The challenge of chiral chemical production lies in the preparation of chiral building blocks in accordance to green chemistry principles. Thus, the aim of this study was to associate the application of whole-cell biocatalysis (plant cells) and the use of environmentally friendly solvents (NADES) for enantioselective preparation of chiral molecules. For that purpose, reduction of 1-(3, 4- dimethylphenyl)ethanone and hydrolysis of ( ± )-1-phenylethyl acetate by carrot root in cholinium-based eutectic mixtures as solvents were successfully conducted. The type of hydrogen bond donor and the amount of water present in NADESs influenced the conversion and/or enantiomeric excess in both enantioselective reactions. In conclusion, inversion of the enantioselectivity exhibited by the biocatalyst towards 1-(3, 4- dimethylphenyl)ethanone was noticed by the addition of different amounts of water to NADES. Overall, the results suggest that NADES possess good biocompatibility with plant cells and can be applied as green reaction medium for plant- mediated bioreduction.