Natural deep eutectic solvents as performance additives for biocatalysis

Erol, Özlem; Hollmann, Frank

doi:10.1016/bs.abr.2020.09.004

Cited by 14 publications

(9 citation statements)

References 89 publications

(53 reference statements)

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“…The choice of the solvent plays thereby a central role in developing future biocatalytic applications. In the past few years, deep eutectic solvents (DESs) have emerged as a new solvent class for biocatalysis − and have been labeled as the ‘solvent of the 21st century’ . The DESs, as first described by Abbot et al, can be formed by mixing a quaternary ammonium salt (e.g., choline chloride (ChCl)), acting as a hydrogen bond acceptor (HBA), with a hydrogen bond donor (HBD, e.g., glycerol and urea).…”

Section: Introductionmentioning

confidence: 99%

Comparison and Validation of Force Fields for Deep Eutectic Solvents in Combination with Water and Alcohol Dehydrogenase

Bittner

Huang

Zhang

et al. 2021

J. Chem. Theory Comput.

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Deep eutectic solvents (DESs) have become popular as environmental-friendly solvents for biocatalysis. Molecular dynamics (MD) simulations offer an in-depth analysis of enzymes in DESs, but their performance depends on the force field chosen. Here, we present a comprehensive validation of three biomolecular force fields (CHARMM, Amber, and OPLS) for simulations of alcohol dehydrogenase (ADH) in DESs composed of choline chloride and glycerol/ethylene glycol with varying water contents. Different properties (e.g., protein structure and flexibility, solvation layer, and H-bonds) were used for validation. For two properties (viscosity and water activity) also experiments were performed. The viscosity was calculated with the periodic perturbation method, whereby its parameter dependency is disclosed. A modification of Amber was identified as the best-performing model for low water contents, whereas CHARMM outperforms the other models at larger water concentrations. An analysis of ADH’s structure and interactions with the DESs revealed similar predictions for Amber and CHARMM.

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Section: Introductionmentioning

confidence: 99%

Comparison and Validation of Force Fields for Deep Eutectic Solvents in Combination with Water and Alcohol Dehydrogenase

Bittner

Huang

Zhang

et al. 2021

J. Chem. Theory Comput.

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“…The use of deep eutectic solvents (DESs) and DES/buffer mixtures as a medium for biocatalytic reactions requires taking into account their effect on the activity and stability of enzymes. Choline chloride-based DESs are in most common use [ 29 , 34 , 35 , 36 , 37 ]. However, chloride ions inhibit the activity of fungal laccases [ 69 ].…”

Section: Resultsmentioning

confidence: 99%

“…In addition, enzymatic reactions proceed under ‘mild’ operating conditions, namely at pH values close to neutral, room temperature, under atmospheric pressure and in the absence of toxic organic solvents and meet the requirements of sustainable chemistry [ 29 , 33 , 34 ]. The use of DESs and water (buffer)/DES mixtures as media for enzymatic reactions is currently reported for a limited range of biocatalysts [ 29 , 33 , 34 , 35 , 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Betaine-Based Deep Eutectic Solvent as a New Media for Laccase-Catalyzed Template-Guided Polymerization/Copolymerization of Aniline and 3-Aminobenzoic Acid

Васильева

Морозова

Shumakovich

et al. 2022

IJMS

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Deep eutectic solvents (DESs) can compensate for some of the major drawbacks of traditional organic solvents and ionic liquids and meet all requirements of green chemistry. However, the potential of their use as a medium for biocatalytic reactions has not been adequately studied. In this work we used the DES betaine-glycerol with a molar ratio of 1:2 as co-solvent for enzymatic template-guided polymerization/copolymerization of aniline (ANI) and 3-aminobenzoic acid (3ABA). The laccase from the basidial fungus Trametes hirsuta and air oxygen served as catalyst and oxidant, respectively. Sodium polystyrene sulfonate (PSS) was used as template. Interpolyelectrolyte complexes of homopolymers polyaniline (PANI) and poly(3-aminobenzoic acid) (P3ABA) and copolymer poly(aniline-co-3-aminobenzoic acid) (P(ANI-3ABA)) were prepared and their physico-chemical properties were studied by UV-Vis and FTIR spectroscopy and cyclic voltammetry. According to the results obtained by atomic force microscopy, PANI/PSS had a granular shape, P(ANI-3ABA)/PSS had a spherical shape and P3ABA/PSS had a spindle-like shape. The copolymer showed a greater antimicrobial activity against Escherichia coli and Staphylcocus aureus as compared with the homopolymers. The minimal inhibitory concentration of the P(ANI-3ABA)/PSS against the gram-positive bacterium S. aureus was 0.125 mg mL−1.

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“…Biocatalytic reactions might be inhibited by the low mass-transfer efficiency and the toxicity of hydrophobic substrates/products toward the biocatalyst (Erol and Hollmann 2021 ; Jung et al 2013 ). It was reported that NADESs can improve the mass transfer efficiency by enhancing the permeability of cell membrane, and alleviate substrate/product inhibition (Xia et al 2020 ).…”

Section: Resultsmentioning

confidence: 99%

Effective asymmetric preparation of (R)-1-[3-(trifluoromethyl)phenyl]ethanol with recombinant E. coli whole cells in an aqueous Tween-20/natural deep eutectic solvent solution

et al. 2021

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Abstract(R)-1-[3-(Trifluoromethyl)phenyl]ethanol ((R)-MTF-PEL) is an important chiral building block for the synthesis of a neuroprotective compound, (R)-3-(1-(3-(trifluoromethyl)phenyl)ethoxy)azetidine-1-carboxamide. In this work, an effective whole-cell-catalyzed biotransformation was developed to produce (R)-MTF-PEL, and its productivity was increased by medium engineering strategy. The recombinant E. coli BL21(DE3)-pET28a(+)-LXCAR-S154Y variant affording carbonyl reductase was adopted for the reduction of 3'-(trifluoromethyl)acetophenone to (R)-MTF-PEL with enantiomeric excess (ee) > 99.9%. The addition of 0.6% Tween-20 (w/v) boosted the bioreduction, because the substrate concentration was increased by 4.0-fold than that in the neat buffer solution. The biocatalytic efficiency was further enhanced by introducing choline chloride: lysine (ChCl:Lys, molar ratio of 1:1) in the reaction medium, because the product yield reached 91.5% under 200 mM substrate concentration in the established Tween-20/ChCl:Lys-containing system, which is the highest ever reported for (R)-MTF-PEL production. The optimal reduction conditions were as follows: 4% (w/v) ChCl:Lys, 12.6 g (DCW)/L recombinant E. coli cells, pH 7.0, 30 ℃ and 200 rpm, reaction for 18 h. The combined strategy of surfactant and NADES has great potential in the biocatalytic process and the synthesis of chiral alcohols.

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Natural deep eutectic solvents as performance additives for biocatalysis

Cited by 14 publications

References 89 publications

Comparison and Validation of Force Fields for Deep Eutectic Solvents in Combination with Water and Alcohol Dehydrogenase

Comparison and Validation of Force Fields for Deep Eutectic Solvents in Combination with Water and Alcohol Dehydrogenase

Betaine-Based Deep Eutectic Solvent as a New Media for Laccase-Catalyzed Template-Guided Polymerization/Copolymerization of Aniline and 3-Aminobenzoic Acid

Effective asymmetric preparation of (R)-1-[3-(trifluoromethyl)phenyl]ethanol with recombinant E. coli whole cells in an aqueous Tween-20/natural deep eutectic solvent solution

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