Asymmetric biocatalytic reduction of ketones using hydroxy-functionalised water-miscible ionic liquids as solvents

Gonzalo, Gonzalo de; Lavandera, Iván; Durchschein, Katharina; Wurm, D.; Faber, Kurt; Kroutil, Wolfgang

doi:10.1016/j.tetasy.2007.10.010

Cited by 78 publications

(43 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…De Gonzalo and coworkers [90] also used hydroxylfunctionalized ionic liquids as cosolvents for the asymmetric reduction of ketones catalyzed by crude ADH A from R. ruber. The dehydrogenase was active in 90 vol% tris-(2-hydroxyethyl)-methylammonium (MeOSO 3 )/10% buffer and in Ammoeng 100, 101, and 102 (quaternary ammonium salts containing polyethyleneglycol substituents).…”

Section: Ionic Liquids As Cosolvent For Aqueous Phase Reactionsmentioning

confidence: 99%

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

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

253

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 Cosolvent For Aqueous Phase Reactionsmentioning

confidence: 99%

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

Gorke

Srienc

Kazlauskas

2010

Biotechnol Bioproc E

253

159

View full text Add to dashboard Cite

show abstract

“…Although both N -alkyl and N -(-hydroxyalkyl) N-methylimidazolium chlorides are destabilizing, terminal hydroxylation of the alkyl chain in the cation allows the IL to effectively suppress the protein destabilization induced by heat and by guanidinium chloride (Lange et al, 2005). de Gonzalo et al (2007) (Hinckley et al, 2002). In fact, these 'Tris-like'-ILs are also made up of chaotropic cations and kosmotropic anions.…”

Section: Design and Use Of Biocompatible Ionic Liquidsmentioning

confidence: 99%

Hofmeister effects: an explanation for the impact of ionic liquids on biocatalysis

Yang

2009

Journal of Biotechnology

363

187

View full text Add to dashboard Cite

“…As previous results have shown that ADHs can be highly stable with hydroxy-functionalised ILs [36], the synthesis of watermiscible hydroxylated imidazole-based ILs was envisaged to use them as: (i) an appropriate co-solvent for the enzymatic reactions, allowing the use of higher substrate concentrations and a simpler recovery of the final products from the reaction mixture through extraction, and (ii) as a possible co-substrate for the ADH-catalysed transformations, allowing its reuse over several cycles and avoiding the employment or formation of 2-propanol that could interfere in the purification of interesting volatile products (Scheme 1).…”

Section: Ionic Liquids In Adh-catalysed Reactionsmentioning

confidence: 66%

“…For instance, an extensive study has been performed on the stability of ADH-A (from Rhodococcus ruber) with various amounts of IL, demonstrating that ADH-A can in fact resist high concentrations of IL and afford reasonable conversions, especially with those that are hydroxy-functionalised [36]. Additionally, LBADH (from Lactobacillus brevis) has been used in the presence of several water-miscible ILs to reduce hardly watersoluble ketones such as 2-nonanone and 2-decanone, and also with an IL in a two-phase system to efficiently achieve the bioreduction of 2-octanone due to favourable partition coefficients of the co-substrate (2-propanol) utilised and the co-product (acetone) obtained [39,40].…”

Section: Ionic Liquids In Adh-catalysed Reactionsmentioning

confidence: 99%

Imidazolium-Based Ionic Liquids as Non-conventional Media for Alcohol Dehydrogenase-Catalysed Reactions

et al. 2013

Self Cite

View full text Add to dashboard Cite

Imidazolium-based ionic liquids were designed and synthesised for their use as non-conventional media in alcohol dehydrogenase (ADH)-catalysed reactions. Screenings with several ADHs and various ketone or alcohol substrates for their selective reductions or oxidations, respectively, showed that when containing up to 50% of the ionic liquid the overall conversion of the reactions could be improved in some cases, while the stereoselectivity of the enzyme remained unaltered. Attempts at using these ionic liquids as co-substrates for the recycling of the nicotinamide cofactor led to promising results, opening a new possibility for a substrate-coupled recycling system.

show abstract

Asymmetric biocatalytic reduction of ketones using hydroxy-functionalised water-miscible ionic liquids as solvents

Cited by 78 publications

References 53 publications

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

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

Hofmeister effects: an explanation for the impact of ionic liquids on biocatalysis

Imidazolium-Based Ionic Liquids as Non-conventional Media for Alcohol Dehydrogenase-Catalysed Reactions

Contact Info

Product

Resources

About