gem‐Difluorocarbadisaccharides: Restoring the exo‐Anomeric Effect |
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| Authors: | Bixue Xu Luca Unione Dr. Joao Sardinha Shaoping Wu Prof. Mélanie Ethève‐Quelquejeu Prof. Amelia Pilar Rauter Prof. Yves Blériot Dr. Yongmin Zhang Dr. Sonsoles Martín‐Santamaría Dr. Dolores Díaz Prof. Jesus Jiménez‐Barbero Prof. Matthieu Sollogoub |
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| Affiliation: | 1. Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France);2. Chemical and Physical Biology, CIB‐CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain);3. Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Lisboa (Portugal);4. Université de Poitiers, UMR CNRS 7285, IC2MP, 4, avenue Michel Brunet, 86022 Poitiers Cedex (France);5. Faculty of Pharmacy, Universidad CEU San Pablo, 28668‐Madrid (Spain) |
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| Abstract: | 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 CF2 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 CF2 analogue adopts the natural glycoside conformation, which might provide new avenues for sugar‐based drug design. |
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| Keywords: | anomeric effect conformation analysis fluorine glycosides NMR spectroscopy |
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