Enzyme-mediated transglycosylation of rutinose (6-O-α-l -rhamnosyl-d -glucose) to phenolic compounds by a diglycosidase fromAcremoniumsp. DSM 24697
| Autor: | Lucas Braun, Helena Pelantová, Javier D. Breccia, Vladimír Křen, Michael Kotik, Laura S. Mazzaferro, Gisela Weiz |
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| Rok vydání: | 2018 |
| Předmět: |
0106 biological sciences
Phloroglucinol Biomedical Engineering Bioengineering 01 natural sciences Applied Microbiology and Biotechnology 03 medical and health sciences chemistry.chemical_compound Hesperidin D-Glucose 010608 biotechnology Drug Discovery Moiety Organic chemistry 030304 developmental biology chemistry.chemical_classification 0303 health sciences Hydroquinone Process Chemistry and Technology Glycoside General Medicine Rutinose chemistry Pyrogallol Molecular Medicine Biotechnology |
| Zdroj: | Biotechnology and Applied Biochemistry. 66:53-59 |
| ISSN: | 0885-4513 |
| Popis: | 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-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-l-rhamnopyranosyl-β-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-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 °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 pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds. |
| Databáze: | OpenAIRE |
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