Protecting-Group-Free Solid-Phase Anchoring of Polyphenolic C-Glucosidic Ellagitannins and Synthesis of 1-Alkylamino-Vescalagin Derivatives with Chemspeed’s Fully Automated SYNTHESIZER
The C-glucosidic ellagitannins vescalagin and vescalin are among the plant polyphenols that have been shown to interact with protein targets in a specific manner. This work describes a protecting-group-free method to immobilize these protein-binding natural products on a solid support, and a functionalizing cleavage method, which is adaptable to the solution-phase synthesis of vescal(ag)in derivatives, and which advantageously permitted the preparation of 1-alkylamino derivatives of vescalagin.
Protecting-Group-Free Solid-Phase Anchoring of Polyphenolic C-Glucosidic Ellagitannins and Synthesis of 1-Alkylamino-Vescalagin Derivatives
Céline Douat, Emanuela Berni, Rémi Jacquet, Laurent Pouységu, Denis Deffieux, and Stéphane Quideau*
Université de Bordeaux, Institut des Sciences Moléculaires (UMR-CNRS 5255) and Institut Européen de Chimie et Biologie (IECB), 2 rue Robert Escarpit, 33607 Pessac cedex, France