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Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697
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SYSNO ASEP 0504259 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 Author(s) Mazzaferro, L.S. (AR)
Weiz, G. (AR)
Braun, L. (AR)
Kotík, Michael (MBU-M) RID, ORCID
Pelantová, Helena (MBU-M) ORCID, RID
Křen, Vladimír (MBU-M) RID, ORCID
Breccia, J.D. (AR)Source Title Biotechnology and Applied Biochemistry. - : Wiley - ISSN 0885-4513
Roč. 66, č. 1 (2019), s. 53-59Number of pages 7 s. Language eng - English Country US - United States Keywords alpha-rhamnosyl-beta-glucosidase ; hesperidin ; hydroquinone Subject RIV CE - Biochemistry OECD category Biochemistry and molecular biology R&D Projects LTC17009 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support MBU-M - RVO:61388971 UT WOS 000458289100006 EID SCOPUS 85055577840 DOI 10.1002/bab.1695 Annotation The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-alpha-rhamnosyl-beta-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-alpha-l-rhamnopyranosyl-beta-d-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values <= 6.0. The structure of 4-hydroxyphenyl-beta-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-beta-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 degrees C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pK(a) value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds. Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2020 Electronic address https://iubmb.onlinelibrary.wiley.com/doi/full/10.1002/bab.1695
Number of the records: 1