Phosphonium alkyl PEG sulfate ionic liquids as coating materials for activation of Burkholderia cepacia lipase

Lipases are among the most widely used enzymes applicable for various substrates; however, the slow reactions or poor enantioselective reactions are sometimes obtained. To develop ionic liquid type activating agents for lipase, four types of phosphonium cetyl(PEG)10 sulfate ionic liquids have been synthesized and used as coating materials of Burkholderia cepacia lipase (Lipase PS) through the lyophilization process. Tributyl ([2-methoxy]ethoxymethyl)phosphonium cetyl(PEG)10 sulfate ([P444MEM ][C16 (PEG)10 SO4 ]) (PL1) worked best among them, and PL1-coated lipase PS displayed high reactivity in transesterification of broad types of secondary alcohols using vinyl acetate as an acylating reagent with perfect enantioselectivity (E > 200). The substrate preference of PL1-PS differs from that of commercial lipase PS or [bdmim] [C16 (PEG)10 SO4 ]-coated lipase (IL1-PS); PL1-PS displayed excellent enantioselectivity in the reaction of 2-chloro-1-phenylethanol with E > 200, though insufficient E values were recorded for lipase PS (E = 12) and IL1-PS (E = 123) for this alcohol. PL1-PS also showed perfect enantioselectivity (E > 200) for the reaction of 1-(pyridin-2-yl)ethanol, while IL1-PS showed E = 130 for this compound. We further succeeded in demonstrating the recyclable use of PL1-PS five times in tributyl(3-methoxypropyl)phosphonium bis(trifluoromethylsulfonyl)amide ([P444PM ][Tf2 N]) as a solvent. Since PL1-PS is easily applicable to 10-20 gram-scaled reactions, it is expected that the IL-coated enzyme might be useful for practical preparation of a wide variety of chiral secondary alcohols.