AMB Express | 2021
Effective asymmetric preparation of (R)-1-[3-(trifluoromethyl)phenyl]ethanol with recombinant E. coli whole cells in an aqueous Tween-20/natural deep eutectic solvent solution
Abstract
( R )-1-[3-(Trifluoromethyl)phenyl]ethanol (( R )-MTF-PEL) is an important chiral building block for the synthesis of a neuroprotective compound, ( R )-3-(1-(3-(trifluoromethyl)phenyl)ethoxy)azetidine-1-carboxamide. In this work, an effective whole-cell-catalyzed biotransformation was developed to produce ( R )-MTF-PEL, and its productivity was increased by medium engineering strategy. The recombinant E. coli BL21(DE3)-pET28a(+) - LXCAR-S154Y variant affording carbonyl reductase was adopted for the reduction of 3 -(trifluoromethyl)acetophenone to ( R )-MTF-PEL with enantiomeric excess (ee)\u2009>\u200999.9%. The addition of 0.6% Tween-20 (w/v) boosted the bioreduction, because the substrate concentration was increased by 4.0-fold than that in the neat buffer solution. The biocatalytic efficiency was further enhanced by introducing choline chloride: lysine (ChCl:Lys, molar ratio of 1:1) in the reaction medium, because the product yield reached 91.5% under 200\xa0mM substrate concentration in the established Tween-20/ChCl:Lys-containing system, which is the highest ever reported for ( R )-MTF-PEL production. The optimal reduction conditions were as follows: 4% (w/v) ChCl:Lys, 12.6\xa0g (DCW)/L recombinant E. coli cells, pH 7.0, 30 ℃ and 200\xa0rpm, reaction for 18\xa0h. The combined strategy of surfactant and NADES has great potential in the biocatalytic process and the synthesis of chiral alcohols.