Design of phosphonium ionic liquids for lipase-catalyzed transesterification

Abe, Yoshikazu; Kude, Keisuke; Hayase, Shuichi; Kawatsura, Motoi; Tsunashima, Katsuhiko; Itoh, Toshiyuki

doi:10.1016/j.molcatb.2007.11.010

Cited by 83 publications

(56 citation statements)

References 26 publications

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“…The IL-coated lipase PS is also commercially available. 23 Mucor javanicus lipase coated with various ILs was found to be more active and more stable than the untreated lipase in aqueous solution, and the activation factors were 1. 180 Lozano et al 181 carried out the enzymatic synthesis of citronellyl esters mediated by Novozym  435, and observed that synthetic activity could be improved up to two-fold by using the IL coating onto lipase; they also found the increase in activity followed the hydrophobicity of …”

Section: Modifying the Solvent Environments Water-in-il Microemulsionsmentioning

confidence: 96%

“…9 All these tunable properties are very important for enzyme stabilization and activation; therefore, many enzymatic reactions have been investigated in different types of ILs. 12,13,16,22 Although some ILs (such as those based on BF 4 − , PF 6 − , and Tf 2 N − ) are less denaturing than organic solvents and high catalytic activity and enantioselectivity have been reported for many reactions, 16,23 many enzymes show the same magnitude of activities in ILs as in conventional organic solvents, which are considerably inferior to those in aqueous solutions. Recently, some ILs have been shown capable of dissolving many substrates that are normally insoluble in organic solvents, such as up to 10-20% (wt) cellulose, >100 g L −1 other carbohydrates (including β-D-glucose, sucrose, lactose, and β-cyclodextrin), ascorbic acid, amino acids, fatty acids and triglycerides.…”

Section: Introductionmentioning

confidence: 99%

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Methods for stabilizing and activating enzymes in ionic liquids—a review

Zhao

2010

J of Chemical Tech & Biotech

339

241

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Ionic liquids (ILs) have evolved as a new type of non-aqueous solvents for biocatalysis, mainly due to their unique and tunable physical properties. A number of recent review papers have described a variety of enzymatic reactions conducted in IL solutions; on the other hand, it is important to systematically analyze methods that have been developed for stabilizing and activating enzymes in ILs. This review discusses the biocatalysis in ILs from two unique aspects (1) factors that impact the enzyme's activity and stability, (2) methods that have been adopted or developed to activate and/or stabilize enzymes in ionic media. Factors that may influence the catalytic performance of enzymes include IL polarity, hydrogen-bond basicity/anion nucleophilicity, IL network, ion kosmotropicity, viscosity, hydrophobicity, the enzyme dissolution, and surfactant effect. To improve the enzyme's activity and stability in ILs, major methods being explored include the enzyme immobilization (on solid support, sol-gel, or CLEA), physical or covalent attachment to PEG, rinsing with n-propanol methods (PREP and EPRP), water-in-IL microemulsions, IL coating, and the design of enzyme-compatible ionic solvents. It is exciting to notice that new ILs are being synthesized to be more compatible with enzymes. To utilize the full potential of ILs, it is necessary to further improve these methods for better enzyme compatibility. This is what has been accomplished in the field of biocatalysis in conventional organic solvents. c 2010 Society of Chemical Industry Keywords: ionic liquid; enzyme activity; enzyme stabilization; immobilization; biocatalysis NOTATION CationsBMIM + = 1-butyl-3-methylimidazolium C 2 OC 1 MIM + = 1-(2-methoxy)ethyl-3-methylimidazolium C 2 OHMIM + = 1-(2-hydroxy)ethyl-3-methylimidazolium EMIM + = 1-ethyl-3-methylimidazolium

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Section: Modifying the Solvent Environments Water-in-il Microemulsionsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Methods for stabilizing and activating enzymes in ionic liquids—a review

Zhao

2010

J of Chemical Tech & Biotech

339

241

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“…this solvent with immobilized BCL were about 2 to 4-fold faster that with immidazolium salts and even slightly faster than in diisopropyl ether [45]. The ionic liquid EMIM(CF 3 SO 3 ) enhanced CALB-catalyzed biodiesel production [46] from triglycerides and methanol.…”

Section: Ionic Liquids As Non-aqueous Solventsmentioning

confidence: 99%

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

252

159

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Ionic liquids, also called molten salts, are mixtures of cations and anions that melt below 100 o C. Typical ionic liquids are dialkylimidazolium cations with weakly coordinating anions such as (MeOSO 3 ) or (PF 6 ). Advanced ionic liquids such as choline citrate have biodegradable, less expensive, and less toxic anions and cations. Deep eutectic solvents are also included in the advanced ionic liquids. Deep eutectic solvents are mixtures of salts such as choline chloride and uncharged hydrogen bond donors such as urea, oxalic acid, or glycerol. For example, a mixture of choline chloride and urea in 1:2 molar ratio liquefies to form a deep eutectic solvent. Their properties are similar to those of ionic liquids. Water-miscible ionic liquids as cosolvents with water enhance the solubility of substrates or products. Although traditional water-miscible organic solvents also enhance solubility, they often inactivate enzymes, while ionic liquids do not. The enhanced solubility of substrates can increase the rate of reaction and often increases the regioor enantioselectivity. Ionic liquids can also be solvents for non-aqueous reactions. In these cases, they are especially suited to dissolve polar substrates. Polar organic solvent alternatives inactivate enzymes, but ionic liquids do not even when they have similar polarities. Besides their solubility properties, ionic liquids and deep eutectic solvents may be greener than organic solvents because ionic liquids are nonvolatile, and can be made from nontoxic components. This review covers selected examples of enzyme catalyzed reaction in ionic liquids that demonstrate their advantages and unique properties, and point out opportunities for new applications. Most examples involve hydrolases, but oxidoreductases and even whole cell reactions have been reported in ionic liquids. © KSBB hÉóïçêÇëW=áçåáÅ=äáèìáÇëI=ÇÉÉé=ÉìíÉÅíáÅ=ëçäîÉåíëI=ÜóÇêçä~ëÉëI=çñáÇçêÉÇìÅí~ëÉëI=éçäóãÉêáò~íáçå= = = = = IONIC LIQUIDS AND DEEP EUTECTIC SOLVENTSIonic liquids, also called molten salts, are mixtures of cations and anions that melt below 100 o C. The low melting point stems from a mismatch in the size of the anion and cation that prevents crystallization. Changing the structures of the anions or cations can tune the polarities and other properties. Even though they are salts, their polarities are only moderate, similar to ethanol. Ionic liquids have negligible vapor pressure. Ionic liquids are viscous, typically 0.1 Pas or more, which is similar to glycerol or honey.The first ionic liquid -ethylammonium nitrate (mp 12 o C) -was reported in 1914 [1], but attracted limited use. The first generation of widely studied ionic liquids used the dialkylimmidazolium and related cations reported in 1982 [2], Fig. 1. Varying the cation structure varied the properties of the ionic liquid. The anions were chloroaluminate or other metal halide anions, which react with water and thus are not suited for biotransformations. The second generation of ionic liquids, discovered a decade later [3], replaced the water r...

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“…Recently, phosphonium-based ILs have been used [124] in the degradation of phenol, esterification, Wittig reaction, Heck reactions, Suzuki cross-coupling reactions, oxidation of benzyl halides [125], etc. Phosphonium tosylates are used as solvents in catalytic hydroformylation reactions; these catalyst systems are noncorrosive and can readily be recovered and reused [126].…”

Section: Applications Of Phosphonium-based Ionic Liquidsmentioning

confidence: 99%

Ammonium- and Phosphonium-Based Ionic Liquid: Green and Reusable Catalysts

Sarda¹,

Wasmatkar²,

Jadhav³

et al. 2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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Recently, the use of ionic liquids (ILs) attracted an increasing interest in the field of organic synthesis because of its mild reaction condition, negligible vapor pressure, solvating ability, and easy recyclability. ILs are used as green reaction media due to their unique chemical and physical properties such as non-volatility, noninflammability, thermal stability, and controlled miscibility. Today, they have a wider scope, playing significant role in reactions as a solvent as well as catalyst. Several reactions have been recently reported using ILs as reaction media and rate enhancers. In chemical and pharmaceutical industries, there is always a demand for

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Design of phosphonium ionic liquids for lipase-catalyzed transesterification

Cited by 83 publications

References 26 publications

Methods for stabilizing and activating enzymes in ionic liquids—a review

Methods for stabilizing and activating enzymes in ionic liquids—a review

Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis

Ammonium- and Phosphonium-Based Ionic Liquid: Green and Reusable Catalysts

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