title: Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization.
abstract: Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing α/β-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.
authors.affiliation: Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Biosciences Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Karel
authors.initials: K
authors.lastname: De Winter
authors.affiliation: Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Biosciences Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Griet
authors.initials: G
authors.lastname: Dewitte
authors.affiliation: Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Biosciences Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Mareike E
authors.initials: ME
authors.lastname: Dirks-Hofmeister
authors.affiliation: Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Biosciences Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Sylvie
authors.initials: S
authors.lastname: De Laet
authors.forename: Helena
authors.initials: H
authors.lastname: Pelantová
authors.forename: Vladimír
authors.initials: V
authors.lastname: Křen
authors.affiliation: Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Biosciences Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Tom
authors.initials: T
authors.lastname: Desmet
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism*; D004355:Drug Stability; D016166:Free Radical Scavengers; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D010636:Phenols / Q000737:chemistry / Q000378:metabolism*; D006005:Phosphorylases / Q000378:metabolism*; D011435:Propyl Gallate / Q000737:chemistry / Q000378:metabolism; D012995:Solubility
chemical_list: D000975:Antioxidants; D016166:Free Radical Scavengers; D006027:Glycosides; D010636:Phenols; D011435:Propyl Gallate; D006005:Phosphorylases
keywords: ABTS; DPPH; antioxidant; glycosylation; phosphorylase