Deep Eutectic Solvents for<i>Candida antarctica</i>Lipase B-Catalyzed Reactions

Gorke, Johnathan T.; Srienc, Friedrich; Kazlauskas, Romas J.

doi:10.1021/bk-2010-1038.ch014

Cited by 35 publications

(20 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ring-opening polymerization of β-propiolactone and ε-caprolactone in BMIM(Tf 2 N) catalyzed by CALB gave molecular weight ~10,000, but other lactones gave only low molecular weight oligomers [67] similar to the result in organic solvents. CALB also catalyzed the polymerization of ε-caprolactone in deep eutectic solvents [68]. .…”

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

Self Cite

249

159

View full text Add to dashboard Cite

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...

show abstract

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

Self Cite

249

159

View full text Add to dashboard Cite

show abstract

“…Their organization is based on associations between a hydrogen bond acceptor (HBA) such as an ammonium halide and a hydrogen‐bond donor (HBD) 2,3 . The possibility to substitute organic solvents and ionic liquids by DESs has been described in various application fields of chemistry such as extraction, synthesis, catalysis, carbon dioxide capture, or electrochemistry 3–13 . In order to better rationalize the DES molecular organization, theoretical and experimental studies have been performed by focusing on reline so known as archetypical DES.…”

Section: Introductionmentioning

confidence: 99%

“…2,3 The possibility to substitute organic solvents and ionic liquids by DESs has been described in various application fields of chemistry such as extraction, synthesis, catalysis, carbon dioxide capture, or electrochemistry. [3][4][5][6][7][8][9][10][11][12][13] In order to better rationalize the DES molecular organization, theoretical and experimental studies have been performed by focusing on reline so known as archetypical DES. Reline is a blend of choline chloride salt (ChCl) and urea molecule (U; see Scheme 1) in molar ratio 1:2.…”

Section: Introductionmentioning

confidence: 99%

Cold‐spray ionization mass spectrometry of the choline chloride‐urea deep eutectic solvent (reline)

et al. 2021

View full text Add to dashboard Cite

Cold‐Spray Ionization mass spectrometry (CSI‐MS) that can be compared to an electrospray ionization (ESI) source acting with a nebulizing gas cooled by liquid nitrogen is used for analyzing reline as Deep Eutectic Solvent (DES). The association of cholinium chloride salts with urea molecules is evidenced in negative CSI‐MS through the chloride adduct formation. The structure of the supramolecular assemblies forming the reline ions that are observed on CSI mass spectra is rationalized by chemical quantum calculations. The theoretical studies indicate that the ionic network organization is only supported by a maximization of hydrogen bonds of the chlorides with the hydroxyl and methyl moieties of the cholinium cations and the amino groups of urea. The studies of gas‐phase fragmentation of the supra‐molecular ionic assemblies detected in CSI‐MS are performed using the in‐source collision‐induced dissociation experiments. The experimental measurements in CSI‐MS, interpreted at the light of the molecular modelization results, suggest that the insertion of urea in adducts of chlorides with cholinium cations does not lead to the most stable ions.

show abstract

“…[1][2][3][4] DESs and the broader ionic liquid (IL) solvent class have potential as reaction media and reactor systems. 2,[5][6][7][8][9] Their tuneable properties, including temperature stability and solvation of drug and catalytic molecules make ILs and DESs preferable to traditional oil/water emulsions. 2,10,11 There have been some reports of ionic liquid (IL) based emulsions (using IL as an additive, or as the oil, or as the polar phase, or even IL in IL emulsions).…”

Section: Introductionmentioning

confidence: 99%