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Molecules 2018, 23(11), 2885; https://doi.org/10.3390/molecules23112885

Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

1
Instituto de Catálisis y Petroleoquímica, CSIC, 28049 Madrid, Spain
2
Centro de Investigación y Asistencia en Tecnología y Diseño del Estado de Jalisco (CIATEJ), Guadalajara 44270, Jalisco, Mexico
3
Center for Cooperative Research in Biosciences, Parque Científico Tecnológico de Bizkaia, 48160 Derio, Biscay, Spain
*
Author to whom correspondence should be addressed.
Received: 17 October 2018 / Revised: 30 October 2018 / Accepted: 1 November 2018 / Published: 5 November 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

The regioselective α-glucosylation of hesperetin was achieved by a transglycosylation reaction catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. using soluble starch as glucosyl donor. By combining mass spectrometry (ESI-TOF) and 2D-NMR analysis, the main monoglucosylated derivative was fully characterized (hesperetin 7-O-α-d-glucopyranoside). In order to increase the yield of monoglucoside, several reaction parameters were optimized: Nature and percentage of cosolvent, composition of the aqueous phase, glucosyl donor, temperature, and the concentrations of hesperetin and soluble starch. Under the optimal conditions, which included the presence of 30% of bis(2-methoxyethyl) ether as cosolvent, the maximum concentration of monoglucoside was approximately 2 mM, obtained after 24 h of reaction. To our knowledge, this is the first report of direct glucosylation of hesperetin employing free enzymes instead of whole cells. View Full-Text
Keywords: polyphenols; glycosylation; flavonoids; flavanones; cyclodextrin glucosyltransferase; enzymatic glucosylation; hesperidin; hesperetin polyphenols; glycosylation; flavonoids; flavanones; cyclodextrin glucosyltransferase; enzymatic glucosylation; hesperidin; hesperetin
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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González-Alfonso, J.L.; Míguez, N.; Padilla, J.D.; Leemans, L.; Poveda, A.; Jiménez-Barbero, J.; Ballesteros, A.O.; Sandoval, G.; Plou, F.J. Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase. Molecules 2018, 23, 2885.

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