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Polymerization of (+)-Catechin in a Deep Eutectic Solvent Using a Fungal Laccase: Physicochemical Properties of the Products and Inhibition of α-Glucosidase

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Abstract

Deep eutectic solvents (DESs) are an alternative to traditional organic solvents for enzymatic reactions between compounds with poor solubility. Biocatalytic polymerization of the flavonoid (+)-catechin (CC) was carried out with laccase from the fungus Trametes hirsuta in a DES–buffer mixture (betaine/glycerol 60 vol %–buffer 40 vol %). The conditions for the synthesis of catechin oligomers (oligoCCs) soluble in organic solvents have been selected. According to the data from high-performance liquid chromatography, the oligoCCs had average molecular weights of 10 620 and 2540 g/mol with polydispersity indices of 1.1 and 1.09, respectively. The physicochemical properties of the obtained oligomers were studied via UV-visible, FTIR, 1H and 13C NMR spectroscopy. The resulting oligoCCs inhibited the α-glucosidase activity (IC50 ~ 8 μg/mL).

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Funding

The work was partially supported by the Russian Foundation for Basic Research (project no. 20-08-00104a).

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Authors and Affiliations

  1. Bach Institute of Biochemistry, Federal Research Center “Fundamentals of Biotechnology”, of the Russian Academy of Sciences, 119071, Moscow, Russia

    M. E. Khlupova, O. V. Morozova, I. S. Vasil’eva, G. P. Shumakovich & A. I. Yaropolov

  2. Department of Chemistry, Lomonosov Moscow State University, 119991, Moscow, Russia

    E. A. Zaitseva & V. A. Chertkov

  3. State Research Institute of Chemistry and Technology of Organoelement Compounds, 105118, Moscow, Russia

    A. K. Shestakova

Authors
  1. M. E. Khlupova
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  2. O. V. Morozova
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  3. I. S. Vasil’eva
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  4. G. P. Shumakovich
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  5. E. A. Zaitseva
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  6. V. A. Chertkov
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  7. A. K. Shestakova
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  8. A. I. Yaropolov
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Correspondence to A. I. Yaropolov.

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The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

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Translated by G. Levit

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Khlupova, M.E., Morozova, O.V., Vasil’eva, I.S. et al. Polymerization of (+)-Catechin in a Deep Eutectic Solvent Using a Fungal Laccase: Physicochemical Properties of the Products and Inhibition of α-Glucosidase. Appl Biochem Microbiol 57, 712–718 (2021). https://doi.org/10.1134/S0003683821060065

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