Effect of Oxygen-Containing Functional Groups on Protein Stability in Ionic Liquid Solutions

Turner, Megan B.; Holbrey, John D.; Spear, Scott K.; Pusey, Marc L.; Rogers, Robin D.

doi:10.1021/bk-2005-0902.ch018

Cited by 12 publications

(5 citation statements)

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“…The same IL was further used to establish the codeinone/neopinone equilibriation and the hydration of the neopinone double bond to form oxycodone via bis(acetylacetonato)cobalt (II) catalysis. Turner et al 267 studied the stability of human serum albumin (HSA) in aqueous solutions of ILs by fluorescence and CD spectroscopy, and found the hydroxyl/ether-functionalized imidazolium ILs to be less protein-denaturing than [BMIM]Cl, which was explained due to the likely favorable H-bond interactions between ILs and the protein.…”

Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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“…Studies have shown that enzymes may retain their catalytic activity in IL solutions presumably as a result of structure conservation. − This has led to the development of ILs specifically for use with proteins. , Interestingly, several examples have been found to thermally stabilize proteins, in some instances to over 100 °C. , The effects of adding hydroxyls to short aliphatic chains have been found to increase protein stability in imidazolium-based ILs . ILs have also been shown to be useful for refolding proteins. , It is important to note here, however, that other studies have suggested the denaturation and subsequent inability of enzymes to refold is a result of contact with IL solutions .…”

Section: Introductionmentioning

confidence: 99%

Protein Crystallization Using Room Temperature Ionic Liquids

Pusey

Paley

Turner

et al. 2007

Crystal Growth & Design

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The ionic liquids (ILs) 1-butyl-3-methylimidizolium chloride ([C4mim]Cl), 1-butyl-3-methylimidizolium 2(2-methoxyethoxy)ethylsulfate ([C4mim][MDEGSO4]), and 1-butyl-1-methylpyrollidinium dihydrogenphosphate ([p1,4][DHP]) were tested for their effects on the crystallization of the proteins canavalin, β-lactoglobulin B, xylanase, and glucose isomerase, using a standard high throughput screen. The crystallization experiments were set up with the ILs added to the protein solutions at 0.2 and 0.4 M final concentrations. Crystallization droplets were set up at three protein/precipitant ratios (1:1, 2:1, and 4:1), which served to progressively dilute the effects of the screen components while increasing the equilibrium protein and IL concentrations. Crystals were obtained for all four proteins at a number of conditions where they were not obtained from IL-free control experiments. Over half of the protein−IL combinations tested had more successful outcomes than negative outcomes, where the IL-free crystallization was better than the corresponding IL-containing outcome, relative to the control. One of the most common causes of a negative outcome was solubilization of the protein by the IL, resulting in a clear drop. In one instance, we were able to use the IL-induced solubilizing to obtain β-lactoglobulin B crystals from conditions that gave precipitated protein in the absence of IL. The results suggest that it may be feasible to develop ILs specifically for the task of macromolecule crystallization.

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“…For example, Jiang [20] reported some basic proteins, including lysozyme, cytochrome c, trypsinoge, and α-chymotyypsinogen A, were separated successfully with 1-alkyl-3-methylimidazolium-based ionic liquid. Studies on biocatalysis showed that some imidazolium-based ILs could enhance protein activity and make it more stable [21]. In 2002, scientists found gel media, in some way mimicking a microgravity environment, could reduce density driven convection and sedimentation, which resulted in a significant improvement of crystal order [22,23].…”

Section: Introductionmentioning

confidence: 99%

The crystallization of lysozyme in the system of ionic liquid [BMIm][BF₄]‐water

Dan

et al. 2008

Cryst. Res. Technol.

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Lysozyme crystallization was conducted in the ionic liquid (IL) 1-butyl-3-methylimidizolium tetrafluoroborate ([BMIm][BF 4 ]) with different buffer/IL proportions. It was found that the addition of [BMIm][BF 4 ] could promote the crystallization process, during which more lager single crystals with controllable morphologies could be obtained due to the manageable crystal growth velocity. A probable explanation was proposed based on the influence of the ionic polarization and kinetics in the lysozyme crystallization. Moreover, the transform in coordination number and the relative growth rate of different crystal faces were discussed.

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Effect of Oxygen-Containing Functional Groups on Protein Stability in Ionic Liquid Solutions

Cited by 12 publications

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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Protein Crystallization Using Room Temperature Ionic Liquids

The crystallization of lysozyme in the system of ionic liquid [BMIm][BF₄]‐water

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Effect of Oxygen-Containing Functional Groups on Protein Stability in Ionic Liquid Solutions

Cited by 12 publications

References 0 publications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Protein Crystallization Using Room Temperature Ionic Liquids

The crystallization of lysozyme in the system of ionic liquid [BMIm][BF4]‐water

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The crystallization of lysozyme in the system of ionic liquid [BMIm][BF₄]‐water