Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization
Deep eutectic solvents (DESs) are an alternative to conventional organic solvents in various biocatalytic reactions. Meanwhile, there have been few studies reporting on synthetic reactions in DESs or DES-containing mixtures involving oxidoreductases. In this work, we have studied the effects of seve...
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doaj-faeba58878554ee0a345a200e9817c7d2021-06-01T00:17:18ZengMDPI AGCatalysts2073-43442021-05-011163963910.3390/catal11050639Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product CharacterizationMaria Khlupova0Irina Vasil’eva1Galina Shumakovich2Elena Zaitseva3Vyacheslav Chertkov4Alla Shestakova5Olga Morozova6Alexander Yaropolov7Research Center of Biotechnology of the Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky Ave. 33, bld. 2, 119071 Moscow, RussiaResearch Center of Biotechnology of the Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky Ave. 33, bld. 2, 119071 Moscow, RussiaResearch Center of Biotechnology of the Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky Ave. 33, bld. 2, 119071 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, RussiaDepartment of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, RussiaState Research Institute of Chemistry and Technology of Organoelement Compounds, Shosse Entuziastov 38, 111123 Moscow, RussiaResearch Center of Biotechnology of the Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky Ave. 33, bld. 2, 119071 Moscow, RussiaResearch Center of Biotechnology of the Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky Ave. 33, bld. 2, 119071 Moscow, RussiaDeep eutectic solvents (DESs) are an alternative to conventional organic solvents in various biocatalytic reactions. Meanwhile, there have been few studies reporting on synthetic reactions in DESs or DES-containing mixtures involving oxidoreductases. In this work, we have studied the effects of several DESs based on betaine as the acceptor of hydrogen bonds on the catalytic activity and stability of laccase from the basidial fungus <i>Trametes hirsuta</i> and performed enzymatic polymerization of the flavonoid dihydroquercetin (DHQ, taxifolin) in a DES–buffer mixture containing 60 vol.% of betaine-glycerol DES (molar ratio 1:2). The use of the laccase redox mediator TEMPO enabled an increased yield of DHQ oligomers (oligoDHQ), with a number average molecular weight of 1800 g mol<sup>−1</sup> and a polydispersity index of 1.09. The structure of the synthesized product was studied using different physicochemical methods. NMR spectroscopy showed that oligoDHQ had a linear structure with an average chain length of 6 monomers. A scheme for enzymatic polymerization of DHQ in a DES–buffer mixture was also proposed.https://www.mdpi.com/2073-4344/11/5/639biocatalysisdeep eutectic solventslaccasedihydroquercetin oligomersNMR |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Maria Khlupova Irina Vasil’eva Galina Shumakovich Elena Zaitseva Vyacheslav Chertkov Alla Shestakova Olga Morozova Alexander Yaropolov |
spellingShingle |
Maria Khlupova Irina Vasil’eva Galina Shumakovich Elena Zaitseva Vyacheslav Chertkov Alla Shestakova Olga Morozova Alexander Yaropolov Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization Catalysts biocatalysis deep eutectic solvents laccase dihydroquercetin oligomers NMR |
author_facet |
Maria Khlupova Irina Vasil’eva Galina Shumakovich Elena Zaitseva Vyacheslav Chertkov Alla Shestakova Olga Morozova Alexander Yaropolov |
author_sort |
Maria Khlupova |
title |
Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization |
title_short |
Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization |
title_full |
Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization |
title_fullStr |
Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization |
title_full_unstemmed |
Enzymatic Polymerization of Dihydroquercetin (Taxifolin) in Betaine-Based Deep Eutectic Solvent and Product Characterization |
title_sort |
enzymatic polymerization of dihydroquercetin (taxifolin) in betaine-based deep eutectic solvent and product characterization |
publisher |
MDPI AG |
series |
Catalysts |
issn |
2073-4344 |
publishDate |
2021-05-01 |
description |
Deep eutectic solvents (DESs) are an alternative to conventional organic solvents in various biocatalytic reactions. Meanwhile, there have been few studies reporting on synthetic reactions in DESs or DES-containing mixtures involving oxidoreductases. In this work, we have studied the effects of several DESs based on betaine as the acceptor of hydrogen bonds on the catalytic activity and stability of laccase from the basidial fungus <i>Trametes hirsuta</i> and performed enzymatic polymerization of the flavonoid dihydroquercetin (DHQ, taxifolin) in a DES–buffer mixture containing 60 vol.% of betaine-glycerol DES (molar ratio 1:2). The use of the laccase redox mediator TEMPO enabled an increased yield of DHQ oligomers (oligoDHQ), with a number average molecular weight of 1800 g mol<sup>−1</sup> and a polydispersity index of 1.09. The structure of the synthesized product was studied using different physicochemical methods. NMR spectroscopy showed that oligoDHQ had a linear structure with an average chain length of 6 monomers. A scheme for enzymatic polymerization of DHQ in a DES–buffer mixture was also proposed. |
topic |
biocatalysis deep eutectic solvents laccase dihydroquercetin oligomers NMR |
url |
https://www.mdpi.com/2073-4344/11/5/639 |
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