Production of chiral compound using recombinant Escherichia coli cells co-expressing reductase and glucose dehydrogenase in an ionic liquid/water two phase system

(S)-3-Chloro-1-phenyl-1-propanol ((S)-CPPO) is a useful chiral building block for the synthesis of anti-depressant drugs. The yeast reductase, YOL151W, evidences enantioselective reduction activity, converting 3-chloro-1-phenyl-1-propanone (3-CPP) into (S)-CPPO. Escherichia coli whole cells co-expressing YOL151W and Bacillus subtilis glucose dehydrogenase were employed for the synthesis of CPPO following permeabilization treatment. A reaction system employing these recombinant E. coli whole cells could convert 30 mM 3-CPP enantioselectively into (S)-CPPO. In an effort to enhance substrate solubility and to prevent substrate/product inhibition during the enzyme reaction process, a variety of ionic liquids were tested and [Bmim][NTf2] was ultimately selected for the ionic liquid/water two phase system. Tween 40 was added to accomplish the efficient mixing of the two phases. Using these recombinant E. coli whole cells and the [Bmim][NTf2]/water two phase system, 100 mM (S)-CPPO was generated with an enantiomeric excess of >99%.

Figure optionsDownload as PowerPoint slideHighlights
► We construct E. coli co-expressing yeast reductase YOL151W and B. subtilis GDH.
► The recombinant E. coli whole cells convert 3-CPP exclusively into (S)-CPPO.
► We construct the ionic liquid [Bmim][NTf2]/water system using E. coli cells.
► The reaction system generates 100 mM (S)-CPPO with an enantiomeric excess of 99%.