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Protecting‐Group‐Free Solid‐Phase Anchoring of Polyphenolic C ‐Glucosidic Ellagitannins and Synthesis of 1‐Alkylamino‐Vescalagin Derivatives
Author(s) -
Douat Céline,
Berni Emanuela,
Jacquet Rémi,
Pouységu Laurent,
Deffieux Denis,
Quideau Stéphane
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402444
Subject(s) - chemistry , solid phase synthesis , polyphenol , protecting group , combinatorial chemistry , organic chemistry , cleavage (geology) , stereochemistry , biochemistry , peptide , geotechnical engineering , fracture (geology) , engineering , alkyl , antioxidant
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.