Enzymatic Condensation Reactions in Ionic Liquids

Kaftzik, Nicole; Neumann, Sebastian; Kula, Maria‐Regina; Kragl, Udo

doi:10.1021/bk-2003-0856.ch017

Cited by 17 publications

(15 citation statements)

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“…223,224 The amidation of the dipeptide H-Ala-Phe-OH (37, Figure 27) was carried out in [BMIm][MeSO 4 ] containing a trace of water as well as in ACN-DMF-water (71:25:4); the biocatalyst was the peptide amidase from S. maltophilia. 88 A product yield of 15% after 12 h was obtained in both media.…”

Section: Proteasesmentioning

confidence: 92%

Biocatalysis in Ionic Liquids

2007

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Fred van Rantwijk (1943) studied organic chemistry at the Delft University of Technology, where he remained as a staff member. He received his Ph.D. in 1980, for work under the guidance of Professor H. van Bekkum. Since the late 1980s he has been working on the application of enzymes in organic synthesis. His particular research interests are the use of enzymes in nonnatural reactions and nonnatural media, enzyme immobilization, and transformations using multi-enzyme systems.Roger Sheldon (1942) received a Ph.D. in organic chemistry from the University of Leicester (U.K.) in 1967. This was followed by postdoctoral studies with Prof. Jay Kochi in the U.S. From 1969 to 1980 he was with Shell Research in Amsterdam, and from 1980 to 1990 he was R&D Director of DSM Andeno. In 1991 he moved to his present position as Professor of biocatalysis and organic chemistry at the Delft University of Technology (The Netherlands). His primary research interests are in the application of catalytic methodologiesshomogeneous, heterogeneous, and enzymaticsto organic synthesis, particularly in relation to fine chemicals production. He developed the concepts of E factors and atom utilization for assessing the environmental impact of chemical processes.

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Section: Proteasesmentioning

confidence: 92%

Biocatalysis in Ionic Liquids

2007

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“…Adding 0.6% water to the ionic liquid allows the galactosidase to be active and catalyze the synthesis of lactose by condensation of glucose and galactose. The yield of lactose was only 18% [73], but this low yield is largely due to the less favorable equilibrium for formation of glycosides. The requirement to add 0.6% water for galactosidase activity further decreased the equilibrium amount of product.…”

Section: Ionic Liquids As Non-aqueous Solventsmentioning

confidence: 98%

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

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

253

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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“…Another study by Irimescu and Kato on the lipase‐catalyzed acylation of primary amines indicated lower reaction rates in ILs with longer alkyl chains in cations, and the water miscibility of ILs was not a main factor in influencing the reaction rate. Some studies also obtained relatively high enzyme activities in hydrophilic ILs (such as [BMIM][BF 4 ], [EMIM][BF 4 ], [BMIM][OTf] and [MMIM][MeSO 4 ]) . The Bruce group evaluated the activities of proteases (chymotrypsin and subtilisin) dissolved in several protic hydroxylalkylammonium‐based ILs (containing ∼1–2 wt% water), and found that subtilisin was only active in diethanolammonium chloride and chymotrypsin was inactive in these protic ILs.…”

Section: Specific Ion Effect Of Ils On Protein Structures and Enzyme mentioning

confidence: 99%

Protein stabilization and enzyme activation in ionic liquids: specific ion effects

Zhao

2015

J of Chemical Tech & Biotech

251

192

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There are still debates on whether the hydration of ions perturbs the water structure, and what is the degree of such disturbance; therefore, the origin of Hofmeister effect on protein stabilization continues being questioned. For this reason, it is suggested to use the ‘specific ion effect’ instead of other misleading terms such as Hofmeister effect, Hofmeister series, lyotropic effect, and lyotropic series. In this review, we firstly discuss the controversial aspect of inorganic ion effects on water structures, and several possible contributors to the specific ion effect of protein stability. Due to recent overwhelming attraction of ionic liquids (ILs) as benign solvents in many enzymatic reactions, we further evaluate the structural properties and molecular-level interactions in neat ILs and their aqueous solutions. Next, we systematically compare the specific ion effects of ILs on enzyme stability and activity, and conclude that (a) the specificity of many enzymatic systems in diluted aqueous IL solutions is roughly in line with the traditional Hofmeister series albeit some exceptions; (b) however, the specificity follows a different track in concentrated or neat ILs because other factors (such as hydrogen-bond basicity, nucelophilicity, and hydrophobicity, etc) are playing leading roles. In addition, we demonstrate some examples of biocatalytic reactions in IL systems that are guided by the empirical specificity rule.

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Enzymatic Condensation Reactions in Ionic Liquids

Cited by 17 publications

References 0 publications

Biocatalysis in Ionic Liquids

Biocatalysis in Ionic Liquids

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

Protein stabilization and enzyme activation in ionic liquids: specific ion effects

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