Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

0504259 - MBÚ 2020 RIV US eng J - Journal Article
Mazzaferro, L.S. - Weiz, G. - Braun, L. - Kotík, Michael - Pelantová, Helena - Křen, Vladimír - Breccia, J.D.
Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697.
Biotechnology and Applied Biochemistry. Roč. 66, č. 1 (2019), s. 53-59. ISSN 0885-4513. E-ISSN 1470-8744
R&D Projects: GA MŠMT LTC17009
Institutional support: RVO:61388971
Keywords : alpha-rhamnosyl-beta-glucosidase * hesperidin * hydroquinone
OECD category: Biochemistry and molecular biology
Impact factor: 1.638, year: 2019
Method of publishing: Limited access
https://iubmb.onlinelibrary.wiley.com/doi/full/10.1002/bab.1695

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.
Permanent Link: http://hdl.handle.net/11104/0295932