Improving β-glucosidase biocatalysis with deep eutectic solvents based on choline chloride

Xu, Wanjun; Huang, Yi-Kei; Li, Feng; Wang, Dandan; Yin, Man-Ni; Wang, Min; Xia, Zhining

doi:10.1016/j.bej.2018.07.002

Cited by 60 publications

(45 citation statements)

References 52 publications

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“…16,31 The results obtained with polyols agree with literature, for instance, the activity of β-glucosidase was higher when 11 polyols, namely ethylene glycol and propylene glycol, were used as constituent in ChCl based DES. 32 The authors explain that a single constituent molecule may diffuse into the enzyme core causing its denaturation by disrupting intramolecular hydrogen bonds. 32 On the other hand, the formation of hydrogen bonds in DES may prevent its diffusion into the enzyme active centre.…”

Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

“…32 The authors explain that a single constituent molecule may diffuse into the enzyme core causing its denaturation by disrupting intramolecular hydrogen bonds. 32 On the other hand, the formation of hydrogen bonds in DES may prevent its diffusion into the enzyme active centre. 32 As DES are prepared by mixing a salt and a hydrogen-bond donor which may be dissociated upon dissolution into aqueous solution, it is reasonable to assume that the DES effects observed result from the combined action of the two DES components.…”

Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

“…32 On the other hand, the formation of hydrogen bonds in DES may prevent its diffusion into the enzyme active centre. 32 As DES are prepared by mixing a salt and a hydrogen-bond donor which may be dissociated upon dissolution into aqueous solution, it is reasonable to assume that the DES effects observed result from the combined action of the two DES components. 8 A similar study using laccase from Escherichia coli BL21 and the glycerol:cholinium chloride DES (molar ratio 2:1) showed that no laccase activity was detected for DES concentrations above 30% (v/v).…”

Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

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Laccase Activation in Deep Eutectic Solvents

Toledo

Pereira

Freire

et al. 2019

ACS Sustainable Chem. Eng.

106

103

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The research on alternative solvents and co-solvents is a relevant aspect when envisioning the improvement of biocatalytic reactions. Among these solvents and co-solvents, deep eutectic solvents (DES) may be considered as customizable new reaction media for biocatalysis. Accordingly, in this work, sixteen DES aqueous solutions, as well as of the individual DES components at the same conditions have been investigated in laccasecatalyzed reactions. Cholinium-and betaine-based DES formed with polyols at different molar ratio and concentrations were evaluated. The results reported show that in presence of most DES the laccase activity is preserved and, with a particular DES, enhanced up to 200%. Molecular docking studies demonstrated that while most DES components establish hydrogen-bonds with the enzyme amino acids, those that establish stronger interactions with the enzyme (expressed by absolute values of docking affinity energies) lead to an enhanced laccase activity. Finally, the laccase stability was evaluated in additional tests under extreme storage temperatures (60 ºC and -80 ºC). Although no significant protection to high temperatures was afforded by DES, an enhanced laccase activity when stored at low temperatures was found, at least up to 20 days. Combining experimental results and molecular docking this work shows that DES can be designed as co-solvents to improve biocatalytic reactions.

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Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

Section: Effect Of Des Nature and Concentration On The Laccase Activitymentioning

confidence: 99%

See 1 more Smart Citation

Laccase Activation in Deep Eutectic Solvents

Toledo

Pereira

Freire

et al. 2019

ACS Sustainable Chem. Eng.

106

103

View full text Add to dashboard Cite

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“…NADESs are biologically compatible agents, and ChCl-based NADESs have been shown to enhance the Fig. 1 Chemical structures of phytoestrogens, including PUE, DZ, GT, DZe, GTe, MI, and DMI enzyme activity of β-glucosidase (Xu et al 2018). In addition, NADESs enhance the stability and activity of other enzymes, such as CYP79A1 and CYP71E1 (Khodaverdian et al 2018).…”

Section: Introductionmentioning

confidence: 99%

Biocompatible natural deep eutectic solvent-based extraction and cellulolytic enzyme-mediated transformation of Pueraria mirifica isoflavones: a sustainable approach for increasing health-bioactive constituents

Makkliang

Siriwarin

Yusakul

et al. 2021

Bioresour. Bioprocess.

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The presence of specific gut microflora limits the biotransformation of Pueraria mirifica isoflavone (PMI) glycosides into absorbable aglycones, thus limiting their health benefits. Cellulolytic enzyme-assisted extraction (CAE) potentially solves this issue; however, solvent extraction requires recovery of the hydrophobic products. Here, we established the simultaneous transformation and extraction of PMIs using cellulolytic enzymes and natural deep eutectic solvents (NADESs). The NADES compositions were optimized to allow the use of NADESs as CAE media, and the extraction parameters were optimized using response surface methodology (RSM). The optimal conditions were 14.7% (v/v) choline chloride:propylene glycol (1:2 mol ratio, ChCl:PG) at 56.1 °C for the cellulolytic enzyme (262 mU/mL) reaction in which daidzin and genistin were extracted and wholly transformed to their aglycones daidzein and genistein. The extraction of PMIs using ChCl:PG is more efficient than that using conventional solvents; additionally, biocompatible ChCl:PG enhances cellulolytic enzyme activity, catalyzing the transformation of PMIs into compounds with higher estrogenicity and absorbability.

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“…The hydrogen bond network formed between the HBA and HBD of the bio‐based DES was an important factor for improving the biocatalytic efficiency. These results supported that DES maintained an HBA–HBD complex in the reaction system rather than separating into individual components …”

Section: Resultsmentioning

confidence: 99%

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

Huang

Wang

2020

J of Chemical Tech & Biotech

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BACKGROUND Deep eutectic solvents (DESs) derived from bio‐available materials are promising eco‐friendly solvents in the field of biocatalysis. However, the type of bio‐based DES is still limited and its application in bioprocess has not been well‐explored. We adopted a design strategy via the combination of choline and amino acids to synthesize novel bio‐based DESs, aimed to enhance biocatalytic efficacy by exploiting the developed DESs as co‐solvents. RESULTS Various bio‐based DESs were synthesized, where the two components are both bio‐available (choline and amino acids). Their performances in the bioreduction of 2‐chloro‐1‐(3,4‐difluorophenyl)ethanone (CFPO) were subsequently evaluated with recombinant Escherichia coli cells. The efficient asymmetric production of (S)‐2‐chloro‐1‐(3,4‐difluorophenyl)ethanol ((S)‐CFPL) was successfully achieved in a developed choline acetate/lysine (ChAc/Lys)‐containing medium. ChAc/Lys can strengthen coenzyme regeneration and properly improve cell membrane permeability during bioreduction, which account for high conversion. After optimized reaction parameters were conducted in the ChAc/Lys‐buffer system, 87.0% (S)‐CFPL yield was observed with > 99.9% enantiomeric excess (ee) value at 1 mol L−1 CFPO content. The substrate loading in the established ChAc/Lys‐buffer system was increased by 3.3‐fold compared to aqueous medium. This bioprocess was also proved to be feasible at 500 mL preparative‐scale with a satisfactory conversion. CONCLUSION ChAc/Lys bio‐DES is a promising and biocompatible co‐solvent. Introducing ChAc/Lys to the reaction system is an effective strategy for challenging high substrate loading for bioreduction. Our results give a valuable insight for developing green and benign sustainable bio‐DESs for biotransformation. © 2020 Society of Chemical Industry

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Improving β-glucosidase biocatalysis with deep eutectic solvents based on choline chloride

Cited by 60 publications

References 52 publications

Laccase Activation in Deep Eutectic Solvents

Laccase Activation in Deep Eutectic Solvents

Biocompatible natural deep eutectic solvent-based extraction and cellulolytic enzyme-mediated transformation of Pueraria mirifica isoflavones: a sustainable approach for increasing health-bioactive constituents

Design and evaluation of novel bio‐based deep eutectic solvents for highly efficient bioproduction of chiral aryl alcohol

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