Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2019 Jun 11;24(11):2190.
doi: 10.3390/molecules24112190.

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

Fatima Zohra Ibn Majdoub Hassani  1   2 , Saaid Amzazi  3 , Iván Lavandera  4
Affiliations
Review

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

Fatima Zohra Ibn Majdoub Hassani et al. Molecules. .

Abstract

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.

Keywords: asymmetric synthesis; biocatalysis; deep eutectic solvents; oxidoreductases.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Enzymatic toolbox showing the oxidation of 5-hydroxymethylfurfural (HMF) to other valuable products [21].
Figure 1
Figure 1
The effect of deep eutectic solvents (DES) on cell membrane permeability. The cations from the choline chloride and urea that form hydrogen bonds can disrupt the cell membrane, allowing the substrate to enter the cells, so then it can bind to the appropriate enzyme. Finally, the product can be released to the medium.
Scheme 2
Scheme 2
The stereoselectivity inversion in the formation of alcohol 1b based on the type of solvent used. (a) Baker’s yeast cells showed a high stereoselectivity towards the (R) enantiomer when some amount of water was mixed with the DES (choline chloride:glycerol 1:2 mol/mol). (b) A high (S)-enantioselectivity was obtained when pure water was used with that biocatalyst.
Figure 2
Figure 2
Examples of chiral alcohols that were obtained in alcohol dehydrogenase (ADH)-biocatalyzed processes in the presence of DES.
Scheme 3
Scheme 3
The possible diastereoisomers that can be obtained from yeast bioreduction of ketone 10a.
Scheme 4
Scheme 4
Bioconversion of cortisone acetate (13a) to prednisone acetate (13b) via ∆1,2-dehydrogenation mediated by Arthrobacter simplex whole cells in buffer/DES media.
See this image and copyright information in PMC

References

    1. Alonso D.A., Baeza A., Chinchilla R., Guillena G., Pastor I.M., Ramon D.J. Deep eutectic solvents: The organic reaction medium of the century. Eur. J. Org. Chem. 2016:612–632. doi: 10.1002/ejoc.201501197. - DOI
    1. Tavares A.P.M., Rodríguez O., Macedo E.A. New generations of ionic liquids applied to enzymatic biocatalysis. In: Kadokawa J.-I., editor. Ionic Liquids. New Aspects for the Future. IntechOpen; London, UK: 2013. pp. 537–556. - DOI
    1. Hallet J.P., Welton T. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 2. Chem. Rev. 2011;111:3508–3576. doi: 10.1021/cr1003248. - DOI - PubMed
    1. Walden P. Ueber die Molekulargrösse und Elektrische Leitfähigkeit einiger Geschmolzenen Salze. Bull. Russ. Acad. Sci. 1914;8:405–422.
    1. Wilkes J.S., Zaworotko M.J. Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids. J. Chem. Soc. Chem. Commun. 1992:965–967. doi: 10.1039/c39920000965. - DOI

LinkOut - more resources