Laccase-catalyzed dimerization of glycosylated lignols
| Autor: | Daniela Monti, Sergio Riva, Paolo Gavezzotti, Ivan Bassanini, Vladimír Křen, Jana Krejzová |
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| Rok vydání: | 2016 |
| Předmět: |
Phenylpropanoid
010405 organic chemistry Stereochemistry Process Chemistry and Technology Disaccharide Substituent Diastereomer Bioengineering Laccase Rutinosidase Biocatalysis Phenylpropanoids Biooxidation Carbohydrate 010402 general chemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Rutinose chemistry.chemical_compound chemistry Proton NMR Organic chemistry Oxidative coupling of methane |
| Zdroj: | Journal of molecular catalysis. B, Enzymatic 134 (2016): 295–301. info:cnr-pdr/source/autori:Ivan Bassanini a-b, Paolo Gavezzotti a, Daniela Monti a, Jana Krejzová c, Vladimír K?en c, Sergio Riva a,/titolo:Laccase-catalyzed dimerization of glycosylated lignols/doi:/rivista:Journal of molecular catalysis. B, Enzymatic (Print)/anno:2016/pagina_da:295/pagina_a:301/intervallo_pagine:295–301/volume:134 |
| ISSN: | 1381-1177 |
| Popis: | Phenylpropanoid glucosides (PPGs) are naturally occurring and bioactive phenolic derivatives, largely distributed in plants. In this work different PPGs have been chemically or enzymatically synthesized from the lignols coniferyl and p -coumaryl alcohols as substrates for a laccase-catalyzed oxidative coupling. The biooxidation of these PPGs has been investigated here and novel dihydrobenzofuran-based structurally modified analogues have been isolated and characterized. Specifically, the presence of a carbohydrate moiety increased the water solubility of these compounds and reduced the number of dimeric products, as pinoresinol-like structures could not be formed. Looking for a possible sugar-promoted stereochemical enrichment of the obtained diastereomeric mixtures of dimers, different carbohydrate moieties ( d -glucose, l -glucose and the disaccharide rutinose) were considered and the respective d.e. values of the dimeric products were measured by 1 H NMR and HPLC. However, it was found that the sugar substituent had a minor effect on the stereochemical outcome of the radical coupling reactions, the best measured result being a d.e. value of 21%. |
| Databáze: | OpenAIRE |
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