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Laccase-Catalyzed Dimerization of Piceid, a Resveratrol Glucoside, and its Further Enzymatic Elaboration
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SYSNO ASEP 0445863 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Laccase-Catalyzed Dimerization of Piceid, a Resveratrol Glucoside, and its Further Enzymatic Elaboration Author(s) Gavezzotti, P. (IT)
Bertacchi, F. (IT)
Fronza, G. (IT)
Křen, Vladimír (MBU-M) RID, ORCID
Monti, D. (IT)
Riva, S. (IT)Source Title Advanced Synthesis & Catalysis. - : Wiley - ISSN 1615-4150
Roč. 357, č. 8 (2015), s. 1831-1839Number of pages 9 s. Language eng - English Country DE - Germany Keywords glycosidase ; laccase ; piceid Subject RIV CC - Organic Chemistry R&D Projects LD13041 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Institutional support MBU-M - RVO:61388971 UT WOS 000355235700023 DOI 10.1002/adsc.201500185 Annotation The laccase-catalyzed oxidation of piceid, the 3-beta-D-glucopyranosyl derivative of the stilbenic phytoalexin resveratrol, allowed isolation of the corresponding beta-5 like trans-dehydrodimer in good yield (45%) avoiding chromatography. This compound was then submitted to the action of a small library of commercially available hydrolases. While the cellulase from Trichoderma viride was able to fully hydrolyze the diglycosylated dimer to give the corresponding beta-5 like trans-dehydrodimer of resveratrol, the beta-glucosidase from almonds allowed the isolation of a monoglycosylated intermediate in reasonable yield. The diastereoisomers and the enantiomers of the isolated dimeric products were separated using a semi-preparative chiral column. The basic antioxidant properties of these new dimers have been determined. Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2016
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