CO 2 -expanded bio-based liquids as novel solvents for enantioselective biocatalysis

Novozym 435: the “perfect” lipase immobilized biocatalyst?

“…N435 was used as an example of the use of CO 2 -expanded bio-based liquids. 321 The model reaction was the resolution of rac-1-adamantylethanol via esterification, which failed using standard solvents but gave very good results using CO 2 -expanded methyltetrahydrofuran (enantiospecificity was 200).…”

Modulating Biocatalytic Activity toward Sterically Bulky Substrates in CO2-Expanded Biobased Liquids by Tuning the Physicochemical Properties

“…33,34 However, as there has been no studies on the solvent properties of CO 2expanded MeTHF reported, the biocatalytic behavior in this novel medium has not yet been addressed. 29 In the present study, by using 1-adamantylethanol 1a as a challenging bulky model substrate, it was found out that CO 2 acts as a crucial trigger for various lipases to catalyze transesterification in a wide range of CO 2 -expanded biobased liquids (Scheme 1). In order to explain our observation, the physicochemical and transport properties of CO 2 -expanded MeTHF were studied both experimentally and by molecular modeling.…”

“…21,29,41,42 It should be noticed that addition of CO 2 to a hydrophilic solvent such as MeOH can increase the nonpolarity and hydrophobicity of this solvent. 29 However, herein, since all conversions in hexane (log P = 3) and biobased solvents (with different log P values, Supplementary Table S1) were low (<4%), the hydrophobicity (log P) alone cannot explain the high reaction conversions obtained in CO 2 -expanded liquids. Without the presence of CO 2 , the enzyme failed to mediate the reaction of bulky 1a even in neat hydrophobic solvents such as hexane (Table 1) or p-cymene ( Figure 2).…”

Lipase-catalyzed enantioselective transesterification of 3-hydroxy-3-(2-thienyl) propanenitrile in liquid carbon dioxide

“…Furthermore, it can be employed at low temperature, which has the potential to enhance the enatioselectivity of enzyme by the low-temperature strategy. Recently, some elegant works have been reported that liquid CO 2 could effectively enhance lipase activity and enantioselectivity in lipase-catalyzed transesterifications (16)(17)(18). These findings encouraged us to further investigate the application of liquid CO 2 in the lipase-catalyzed resolution of racemic pharmaceutical intermediates.…”