10.1002/ejoc.201901251
European Journal of Organic Chemistry
COMMUNICATION
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In conclusion, we developed
a new entry to C-
glycoconjugates bearing clickable functions via the use of readily
accessible N,N’-disubstituted barbituric acids. Experimentally
simple and environmentally friendly, the Knoevenagel
condensation was performed in water onto reducing sugars
without the need for any protecting groups. Mono, homo-bis, and
hetero-bis clickable carbohydrates have been designed and
prepared according to an unprecedented modular and tunable
ligation method. We also demonstrated that this process can be
extended to the preparation of galactose-based glycoclusters
interacting with PNA lectin. We believe this work is a significant
contribution to the field of glycosciences, providing a versatile
ligation platform that are synthetically accessible to a wide range
of researchers. By the way, application of this methodology brings
a new opportunity for the modification of aldehyde-containing
materials.
Acknowledgements
This work has been partially supported by CNRS, Université
Grenoble Alpes, the Labex ARCANE and CBH-EUR-GS (ANR-
17-EURE-0003), Glyco@Alps project (ANR-15-IDEX-02) and
Polynat Carnot Institute (No. 16-CARN-025-01). We thank Emilie
Gillon for her help in ITC measurements and ICMG FR 2607
platform (NMR, mass spectrometry) for the structural analyses.
Keywords: carbohydrates • Knoevenagel condensation •
barbituric acids • click chemistry • glycoclusters
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