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"Water-like" Dual-Functionalized Ionic Liquids for Enzyme Activation.

ABSTRACT: By mimicking the water structure to improve the enzyme activity, we designed imidazolium (Im)-based ionic liquids (ILs) functionalized with both ether and tert-alcohol groups (e.g., [CH3(OCH2CH2) n -Im-t-BuOH][Tf2N]). This unique combination of the "water-like" structure enabled very high transesterification (synthetic) activities for immobilized lipase B from Candida antarctica, which are up to 2-4 folds higher than nonfunctionalized "classical" ionic liquids (such as [BMIM][Tf2N]) and up to 40-100% higher than diisopropyl ether and tert-butanol. Fluorescence emission spectra confirmed the general protein structural preservation in these tailored ionic solvents. In addition, functionalized ILs showed high thermal stabilities, which are comparable with diisopropyl ether but much higher than tert-butanol.

SUBMITTER: Zhao H

PROVIDER: S-EPMC6751713 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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"Water-like" Dual-Functionalized Ionic Liquids for Enzyme Activation.

Zhao Hua H Harter Glenn A GA Martin Caden J CJ

ACS omega 20190904 12

By mimicking the water structure to improve the enzyme activity, we designed imidazolium (Im)-based ionic liquids (ILs) functionalized with both ether and tert-alcohol groups (e.g., [CH3(OCH2CH2) n -Im-t-BuOH][Tf2N]). This unique combination of the "water-like" structure enabled very high transesterification (synthetic) activities for immobilized lipase B from Candida antarctica, which are up to 2-4 folds higher t ...[more]

PMID: 31552369

Similar Datasets

Dual Ionic and Organic Nature of Ionic Liquids.

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| S-EPMC4726069 | biostudies-literature

Evaluation of Ionic Liquids and Ionic Liquids Active Pharmaceutical Ingredients Inhibition in Elastase Enzyme Activity.

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Unexpected Intrinsic Lability of Thiol-Functionalized Carboxylate Imidazolium Ionic Liquids.

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Surface Enrichment in Equimolar Mixtures of Non-Functionalized and Functionalized Imidazolium-Based Ionic Liquids.

Project description:For equimolar mixtures of ionic liquids with imidazolium-based cations of very different electronic structure, we observe very pronounced surface enrichment effects by angle-resolved X-ray photoelectron spectroscopy (XPS). For a mixture with the same anion, that is, 1-methyl-3-octylimidazolium hexafluorophosphate+1,3-di(methoxy)imidazolium hexafluorophosphate ([C8 C1 Im][PF6 ]+[(MeO)2 Im][PF6 ]), we find a strong enrichment of the octyl chain-containing [C8 C1 Im]+ cation and a corresponding depletion of the [(MeO)2 Im]+ cation in the topmost layer. For a mixture with different cations and anions, that is, [C8 C1 Im][Tf2 N]+[(MeO)2 Im][PF6 ], we find both surface enrichment of the [C8 C1 Im]+ cation and the [Tf2 N]- (bis[(trifluoromethyl)sulfonyl]imide) anion, while [(MeO)2 Im]+ and [PF6 ]- are depleted from the surface. We propose that the observed behavior in these mixtures is due to a lowering of the surface tension by the enriched components. Interestingly, we observe pronounced differences in the chemical shifts of the imidazolium ring signals of the [(MeO)2 Im]+ cations as compared to the non-functionalized cations. Calculations of the electronic structure and the intramolecular partial charge distribution of the cations contribute to interpreting these shifts for the two different cations.

| S-EPMC6175172 | biostudies-other

Acid Catalysis with Alkane/Water Microdroplets in Ionic Liquids.

Project description:Ionic liquids are composed of an organic cation and a highly delocalized perfluorinated anion, which remain tight to each other and neutral across the extended liquid framework. Here we show that n-alkanes in millimolar amounts enable a sufficient ion charge separation to release the innate acidity of the ionic liquid and catalyze the industrially relevant alkylation of phenol, after generating homogeneous, self-stabilized, and surfactant-free microdroplets (1-5 μm). This extremely mild and simple protocol circumvents any external additive or potential ionic liquid degradation and can be extended to water, which spontaneously generates microdroplets (ca. 3 μm) and catalyzes Brönsted rather than Lewis acid reactions. These results open new avenues not only in the use of ionic liquids as acid catalysts/solvents but also in the preparation of surfactant-free, well-defined ionic liquid microemulsions.

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Mechanistic Studies of CO2 Cycloaddition Reaction Catalyzed by Amine-Functionalized Ionic Liquids.

Project description:The homogeneous cycloaddition reaction of CO2 and epichlorohydrin catalyzed by amine-functionalized ionic liquid (AFIL) to yield cyclic carbonate is reported in this study. The AFIL has the dual function of ionic liquid and organic base. The experimental study indicates that AFIL can efficiently catalyze the conversion of CO2 and epichlorohydrin to the product 3-chloro-1,2-propylene. The mechanistic study based on DFT calculations reveals that the imidazolium ring in AFIL primarily catalyzes the ring-opening reaction of epichlorohydrin, while the protonated amine group is responsible for stabilizing the Br- anion in the nucleophilic attack. This study provides a deep insight into the catalytic roles of AFIL and also inspires us to design efficient dual function catalysts for CO2 utilization.

| S-EPMC6747045 | biostudies-literature

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