Asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems by use of recombinant Escherichia coli with intracellular cofactor regeneration

Ionic liquids such as [BMIM][PF6] and [BMIM][NTF] are already known as good alternatives to organic solvents in biphasic biotransformation. Herein, we report about a systematic procedure based on physical properties to identify more commercially available ionic liquids exhibiting the potential to improve the efficiency of whole cell biocatalyses. This approach resulted in the identification of seven other water immiscible ionic liquids. These ionic liquids were rated by their biocompatibility, their substrate- and product-specific distribution coefficients and by for example performed asymmetric reductions of several prochiral ketones. With the use of a recombinant Escherichia coli as biocatalyst, overproducing a Lactobacillus brevis alcohol dehydrogenase and a Mycobacterium vaccae N10 formate dehydrogenase for cofactor regeneration, the great potential of asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems were demonstrated in simple batch processes.

Figure optionsDownload as PowerPoint slide

Ethyl (S)-4-chloro-3-hydroxybutyrateC6H11ClO3Ee >99.7%[α]D20=-14 neatSource of chirality: asymmetric whole cell biocatalysis with ionic liquids

(S)-α-Chloro-1-phenylethanolC8H9ClOEe >99.7%[α]D20=+48 (c 2.8, cyclohexane)Source of chirality: asymmetric whole cell biocatalysis with ionic liquids