Enzyme-mediated free radical polymerization of acrylamide in deep eutectic solvents

Sánchez-Leija, Regina J.; Torres-Lubián, Román; Reséndiz-Rubio, A.; Luna‐Bárcenas, Gabriel; Mota‐Morales, Josué D.

doi:10.1039/c5ra27468k

Cited by 43 publications

(25 citation statements)

References 68 publications

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“…To date, in the field of redox biocatalysis, DESs have been explored by using whole cells and isolated ketoreductases (KREDs) and alcohol dehydrogenases (ADHs), as well as in bio‐oxidations mediated by ADHs, heme‐dependent enzymes, laccases, or catalases . Due to the good biocompatibility of DESs and their promotion of increased cell permeability, redox reactions catalyzed by whole cells show higher conversion and stability .…”

Section: Introductionmentioning

confidence: 99%

Modeling Alcohol Dehydrogenase Catalysis in Deep Eutectic Solvent/Water Mixtures

Huang

Bittner

Marı́a³

et al. 2019

ChemBioChem

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The use of oxidoreductases (EC1) in non‐conventional reaction media has been increasingly explored. In particular, deep eutectic solvents (DESs) have emerged as a novel class of solvents. Herein, an in‐depth study of bioreduction with an alcohol dehydrogenase (ADH) in the DES glyceline is presented. The activity and stability of ADH in mixtures of glyceline/water with varying water contents were measured. Furthermore, the thermodynamic water activity and viscosity of mixtures of glyceline/water have been determined. For a better understanding of the observations, molecular dynamics simulations were performed to quantify the molecular flexibility, hydration layer, and intraprotein hydrogen bonds of ADH. The behavior of the enzyme in DESs follows the classic dependence of water activity (aW) in non‐conventional media. At low aW values (<0.2), ADH does not show any activity; at higher aW values, the activity was still lower than that in pure water due to the high viscosities of the DES. These findings could be further explained by increased enzyme flexibility with increasing water content.

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Section: Introductionmentioning

confidence: 99%

Modeling Alcohol Dehydrogenase Catalysis in Deep Eutectic Solvent/Water Mixtures

Huang

Bittner

Marı́a³

et al. 2019

ChemBioChem

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“…A number of types of radical polymerizations have been shown to be successful including enzyme‐mediated, [ 13 ] ATRP, [ 14 ] heterogeneous FRP, [ 15 ] photoinitiated FRP, [ 10,16 ] and free‐radical frontal polymerization. [ 17 ] The success of previous radical polymerizations combined with the realization that the presence of a DES changes the behavior of free‐radical frontal polymerization, [ 17 ] leads one to believe that the DES itself has an impact on the FRP.…”

Section: Intensity [Mw Cm−2] Aa Maa Initial Rate [Min−1] Maximum Convmentioning

confidence: 99%

Kinetic Studies of Photopolymerization of Monomer‐Containing Deep Eutectic Solvents

Fazende

Gary

Mota‐Morales

2020

Macro Chemistry & Physics

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The kinetics of photopolymerization in deep eutectic solvents (DESs) is investigated through real‐time Fourier transform‐infrared spectrometry (RT‐FTIR). The systems of this study are choline chloride (ChCl) DESs made of acrylic acid and methacrylic acid (DES monomers) and a nonreactive analog isobutyric acid (IBA). The DES consisting of the analog also contains the monomer methyl methacrylate (MMA). Analysis of the evolution of conversion indicates dramatic increase in polymerization rate when comparing the polymerization of the DES monomers to pure monomer polymerization. A significant increase in polymerization rate is also seen in the systems that include a methyl ester derivative of the hydrogen bond donor monomer (e.g., MMA) in a nonpolymerizable DES (e.g., IBA−ChCl). It is proposed that the increased solvent viscosity, preorganization due to hydrogen bonding, and the polarity of the DES around the monomers play a role in the enhancement of the polymerization rate.

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“…The concentrations of ChCl:Ur and ChCl:Gly were fixed to 80% v/v when used in the reaction media for acrylamide polymerization to protect the hydrogen bonding network in the hydrated medium while decreasing the viscosity of these solvents. Also, a homogenous mixture was obtained throughout the process [24].…”

Section: Applications Of Deep Eutectic Solvents To Oxidoreductase-mentioning

confidence: 99%

The Versatile Applications of DES and Their Influence on Oxidoreductase-Mediated Transformations

2019

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In the last decade, new types of solvents called deep eutectic solvents (DES) have been synthesized and commercialized. Among their main advantages, they can be eco-friendly and are easy to synthesize at different molar ratios depending on the desired solvent properties. This review aims to show the different uses of DES in some relevant biocatalytic redox reactions. Here we analyze oxidoreductase-mediated transformations that are performed in the presence of DES and compare them with the ones that avoided those solvents. DES were found to present advantages such as the increase in the product yield and enantiomeric excess in many reactions.

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Enzyme-mediated free radical polymerization of acrylamide in deep eutectic solvents

Abstract: The enzyme-mediated free radical polymerization of acrylamide was performed in nearly non-aqueous DES, which allowed the exploration of higher and lower temperatures that in aqueous media.

Cited by 43 publications

References 68 publications

Modeling Alcohol Dehydrogenase Catalysis in Deep Eutectic Solvent/Water Mixtures

Modeling Alcohol Dehydrogenase Catalysis in Deep Eutectic Solvent/Water Mixtures

Kinetic Studies of Photopolymerization of Monomer‐Containing Deep Eutectic Solvents

The Versatile Applications of DES and Their Influence on Oxidoreductase-Mediated Transformations

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