Abstract

A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated: very rapid transesterification of secondary alcohols was accomplished when IL1-PS was used as catalyst in tributyl((2-methoxyethoxy)methyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) or N-ethyl-N-((2-methoxyethoxy)methyl)-N-methylethanaminium bis(trifluoromethanesulfonyl)amide ([N221MEM][NTf2]) as solvent with excellent enantioselectivity. It was also revealed that ammonium ionic liquid influenced the lipase reactivity more strongly than phosphonium ionic liquids. Increased Kcat value was suggested to be the most important factor at work in IL1-PS in these ionic liquid solvents. The Kcat value of (S)-1-phenyethanol in [N444MEM][NTf2] was similar to that of i-Pr2O, and 1.6-fold acceleration was achieved for (R)-1-phenylethanol. On the other hand, the Km value for (R)-isomer in [N444MEM][NTf2] was slightly larger than the reaction in i-Pr2O, while it was signif...

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