Laccase‐Catalyzed Dimerization of Piceid, a Resveratrol Glucoside, and its Further Enzymatic Elaboration. Issue 8 (15th May 2015)

• Record Type: Journal Article
• Authors: Gavezzotti, Paolo; Bertacchi, Federica; Fronza, Giovanni; Křen, Vladimír; Monti, Daniela; Riva, Sergio
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 8(2015)
• Page Start: 1831
• Page End: 1839
• Publication Date: 2015-05-15
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500185
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The laccase‐catalyzed oxidation of piceid, the 3‐β‐<sc>D</sc>‐glucopyranosyl derivative of the stilbenic phytoalexin resveratrol, allowed isolation of the corresponding β‐5 like <italic>trans</italic>‐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 <italic>Trichoderma viride</italic> was able to fully hydrolyze the diglycosylated dimer to give the corresponding β‐5 like <italic>trans</italic>‐dehydrodimer of resveratrol, the β‐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.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgjng09032" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>