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N , N′ ‐Disubstituted Barbituric Acid: A Versatile and Modular Multifunctional Platform for Obtaining β‐ C ‐Glycoconjugates from Unprotected Carbohydrates in Water
Author(s) -
Portier François,
Solier Justine,
Halila Sami
Publication year - 2019
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.201901251
Subject(s) - glycoconjugate , barbituric acid , knoevenagel condensation , chemistry , combinatorial chemistry , urea , organic chemistry , biochemistry , catalysis
Direct access to non‐hydrolyzable glycoconjugates is highly mandatory for stabilizing their intrinsic biological or physical‐chemistry properties in the surrounding environment. Here, a simple and versatile approach for the preparation of multifunctional clickable β‐ C ‐glycoconjugates has been developed. Readily accessible N , N′ ‐disubstituted barbituric acids have been synthesized and ligated in water to the reducing end of unprotected carbohydrates via Knoevenagel condensation. Additionally, divalent glycoclusters have been built from bis‐urea backbones and showed ability to interact with a model lectin, the peanut agglutinin . This concept can be readily adapted for the preparation of other C ‐glycoconjugates applicable in diverse area of glycosciences.