Oxidative Polymerization of Phenolic Glycosides by Peroxidase

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  • ペルオキシダーゼによるフェノール性配糖体の酸化重合

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Abstract

Oxidative polymerization of phenolic glucosides catalyzed by horseradish peroxidase (HRP) was reviewed. Hydroquinone β-glucoside (arbutin, β-Arb) and hydroquinone α-glucoside (α-Arb) were polymerized similarly responding to the addition of H2O2. A calculated model reproduced successfully most of the experimental results: An increase of the polymer with a decrease of the monomer and a temporal accumulation of the dimer. The polymers had linkages at the 3´- and 5´-positions of hydroquinone moieties and abundant polymerization degrees of 7-17. Dimers emitted fluorescence and absorbed a wider UV region. Polymers carrying heterogeneous side residues were synthesized through two successive enzyme reactions, glycosylation and subsequent polymerization. A novel glycoside was also synthesized by the coupling of β-Arb and 2,5-dihydroxybenzoic acid followed by spontaneous intramolecluar esterification.

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