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gem ‐Difluorocarbadisaccharides: Restoring the exo ‐Anomeric Effect
Author(s) -
Xu Bixue,
Unione Luca,
Sardinha Joao,
Wu Shaoping,
EthèveQuelquejeu Mélanie,
Pilar Rauter Amelia,
Blériot Yves,
Zhang Yongmin,
MartínSantamaría Sonsoles,
Díaz Dolores,
JiménezBarbero Jesus,
Sollogoub Matthieu
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201405008
Subject(s) - anomer , anomeric effect , chemistry , stereochemistry , glycobiology , computational chemistry , biochemistry , glycan , glycoprotein
Molecular mimicry is an essential part of the development of drugs and molecular probes. In the chemical glycobiology field, although many glycomimetics have been developed in the past years, it has been considered that many failures in their use are related to the lack of the anomeric effects in these analogues. Additionally, the origin of the anomeric effects is still the subject of virulent scientific debates. Herein, by combining chemical synthesis, NMR methods, and theoretical calculations, we show that it is possible to restore the anomeric effect for an acetal when replacing one of the oxygen atoms by a CF 2 group. This result provides key findings in chemical sciences. On the one hand, it strongly suggests the key relevance of the stereoelectronic component of the anomeric effect. On the other hand, the CF 2 analogue adopts the natural glycoside conformation, which might provide new avenues for sugar‐based drug design.