Hydrolase-catalyzed biotransformations in deep eutectic solvents

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

doi:10.1039/b716317g

Cited by 460 publications

(355 citation statements)

References 30 publications

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“…Compared to other publications using DES as co-solvent in the biocatalysis, many delightful results exerted on the improvement of reaction rate, not the enantioselectivity. For instance, Gorke et al (2008) reported that the co-solvent DES (ChCl/glycerol) had a great influence on the activity but not on the enantioselectivity in the catalysis of styrene oxide by epoxide hydrolase. Moreover, our previous work also indicated that the addition of DES, ChCl/urea, can improve the catalytic activity of Acetobacter sp.…”

Section: The Effects Of Des Concentration On Epoxide Catalysis By Mehsmentioning

confidence: 99%

“…Up to now, DESs have exhibited their application potential because of the advantages of low cost, environmental friendliness, low vapor pressure, low melting point and easy degradation (Flores-Ferrándiz and Chinchilla 2017;Lobo et al 2012a, b). In fact, many reports have shown that deep eutectic solvents can be employed in dissolution and separation (Lu et al 2016;Radošević et al 2016), organic synthesis (Gore et al 2011), electrochemistry (Zhang et al 2012) and catalytic reactions (Cao et al 2016;Gorke et al 2008;Harifi-Mood et al 2017;Xu et al 2015a;Yang and Duan 2016). DESs can be used as not only the co-solvent but also the main reaction medium.…”

Section: Introductionmentioning

confidence: 99%

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The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Peng

Zhao

et al. 2018

Bioresour. Bioprocess.

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Background: Deep eutectic solvents have attracted considerable attention in numerous fields. There is little information on mung bean epoxide hydrolase-catalyzed epoxides in deep eutectic solvent-containing system. Results:Adding deep eutectic solvents with hydrogen bond donor of acids to phosphate buffer resulted in an obvious decrease in the optical purity of product; nevertheless, the relative slight change was observed by the addition of the deep eutectic solvents with hydrogen bond donor of alcohols and urea. Of the tested deep eutectic solvents, 10% additional amount of choline chloride/trithylene glycol can cause a significant improvement in the enantiopurity of product, from 83.2 ± 1.3% to 87.9 ± 0.3%. Moreover, with the increase in the addition amount of choline chloride/ triethylene glycol from 10 to 30%, the enantiomeric excess of product enhanced from 87.9 to 94%, but a decline of product yield was observed. Finally, the evaluation of enzyme stability showed that the additional amount from 10% to 30% was not beneficial to the activity recovery. Conclusion:In short, adding choline chloride/triethylene glycol contributes to the improvement in the optical purity of (R)-1-phenyl-1, 2-ethanediol in the catalysis of styrene oxide by mung bean epoxide hydrolases; meanwhile, the enzyme immobilization could be essential.

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Section: The Effects Of Des Concentration On Epoxide Catalysis By Mehsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Peng

Zhao

et al. 2018

Bioresour. Bioprocess.

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“…Compare to IL, DES display many advantages such as a low price, a very easy preparation without any purification steps (they are simply prepared by mixing the components), and most of them are biodegradable (Durand, Lecomte, Villeneuve, 2013). Thus, the number of publications dedicated to their use has considerably increased in many fields of research such as metal recovery, gas purification, catalysis, chemical fixation of CO 2 (Li et al, 2008;Su et al, 2009), extraction of phytochemicals from plant material (Dai et al, 2013;Nam et al, 2015) or green solvents for biocatalysis (Alemán et al, 2015;Durand et al,2012;Durand, Lecomte, Baréa, 2013;Gorke et al, 2008;Lindberg et al, 2010;Maugeri et al, 2013;Zhao et al, 2011Zhao et al, , 2013. Recently, the term Natural Deep Eutectic Solvents (NADES) was introduced in literature as a new subfamily of LTTM, to label any mixture combining molecules abundantly present in the cellular constituents (e.g.…”

Section: Lttm a New Family Of Promising Green Mediamentioning

confidence: 99%

Are emerging deep eutectic solvents (DES) relevant for lipase-catalyzed lipophilizations?

Durand

Lecomte

Villeneuve

2015

OCL

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-With the recent interest on green chemistry, the scientists have focused on developing new and more efficient solvents to carry out enzymatic-catalyzed reactions with emphasis on reduced costs, risks and toxicity while improving biodegradability. Among the new available solvents, the multimolecular-based liquids (such as ionic liquids and eutectic solvents) have been the subject of most recent studies. Currently, and mainly due to its environmental and economic features, DES are arousing much interest and curiosity. Regarding the biotransformations with lipases, the so-called "lipophilization" reactions are of major interest. However, they are complex to implement mainly because it is difficult to find a suitable reaction medium. Thus, this review aimed at providing a presentation of these multimolecularbased solvents with general overview of the recent studies dealing with lipase-catalyzed reactions in DES. In addition, emphasis was placed on their strengths and weaknesses, especially with the perspective to be use as efficient and green medium to implement complex and valuable biotransformation such as lipase-catalyzed lipophilizations.Keywords: Low transition temperature mixtures / deep eutectic solvents / Lipase / Lipophilization Résumé -Solvants de type eutectiques profonds : milieux réactionnels adaptés aux réactions de lipophilisation biocatalysées par les lipases ? Depuis le début des années 1990 et l'émergence de la « chimie verte », il est indispensable de concevoir des nouveaux procédés, en particulier enzymatiques, qui mettent l'accent sur la réduction des coûts, des risques et de la toxicité tout en améliorant la biodégradabilité. Les nouveaux solvants de type « liquides multimoléculaires » (tels que les liquides ioniques et les solvants eutectiques) ont fait l'objet de la plupart des études récentes. Actuellement, et principalement en raison de ses atouts environnementaux et économiques, les solvants eutectiques suscitent beaucoup plus d'intérêt et de curiosité. Concernant les biotransformations lipasiques, les réactions dites « de lipophilisation » présentent de nombreux avantages. Cependant, ces réactions sont complexes à mettre en oeuvre, principalement parce qu'il est difficile de trouver un milieu réactionnel adapté. Ainsi, cette revue a pour objectif de fournir une présentation de ces milieux réactionnels avec un aperçu des travaux récents portant sur les réactions lipasiques dans des solvants eutectiques. En outre, l'accent a été mis sur leurs forces et leurs faiblesses, avec la perspective d'être utilisés comme milieu réactionnel « vert » pour mettre en oeuvre des biotransformations complexes telles que les réactions de lipophilisation biocatalysées par les lipases. Mots clés :Mélanges à faible transition de température / solvants eutectiques profonds / lipase / lipophilisation

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“…Gorke et al were the first to use enzymes in DESs and to assess the activity of different hydrolases in choline chloride-urea mixtures. 33 Despite high concentrations of urea, which is a strong hydrogen bond donor and denatures proteins, and the presence of halides, which might inactivate or inhibit the proteins, the enzymes showed good catalytic activity. Furthermore, the conversion of styrene oxide to the corresponding diol with epoxide hydrolase was 20-fold enhanced using choline chloride-urea as a co-solvent (Fig.…”

Section: Biocatalytic Reactionsmentioning

confidence: 99%

“…3). 33 The hydrolysis of epoxides has been studied in more detail by Lindberg et al 80 They investigated the effect of different DESs (1 : 2 mixture of ChCl with urea, ethylene glycol, or glycerol) as co-solvents on the hydrolysis of chiral (1,2)-trans-2-methylstyrene oxide enantiomers by potato EH StEH1 hydrolase. By applying DESs as co-solvents, higher reactant concentrations could be achieved and the regioselectivity could be influenced.…”

Section: Biocatalytic Reactionsmentioning

confidence: 99%

Low melting mixtures in organic synthesis – an alternative to ionic liquids?

2012

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Hydrolase-catalyzed biotransformations in deep eutectic solvents

Abstract: Hydrolases show good catalytic activity in deep eutectic solvents, despite the presence of urea, which can denature enzymes, or alcohols, which can interfere with hydrolase-catalyzed reactions.

Cited by 460 publications

References 30 publications

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

Are emerging deep eutectic solvents (DES) relevant for lipase-catalyzed lipophilizations?

Low melting mixtures in organic synthesis – an alternative to ionic liquids?

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