gem-Difluorocarbadisaccharides: Restoring the exo-Anomeric Effect†
Bixue Xu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
These authors contributed equally to this work.
Search for more papers by this authorLuca Unione
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
These authors contributed equally to this work.
Search for more papers by this authorDr. Joao Sardinha
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Lisboa (Portugal)
Search for more papers by this authorShaoping Wu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorProf. Mélanie Ethève-Quelquejeu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorProf. Amelia Pilar Rauter
Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Lisboa (Portugal)
Search for more papers by this authorProf. Yves Blériot
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Université de Poitiers, UMR CNRS 7285, IC2MP, 4, avenue Michel Brunet, 86022 Poitiers Cedex (France)
Search for more papers by this authorDr. Yongmin Zhang
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorDr. Sonsoles Martín-Santamaría
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Faculty of Pharmacy, Universidad CEU San Pablo, 28668-Madrid (Spain)
Search for more papers by this authorDr. Dolores Díaz
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Prof. Jesus Jiménez-Barbero
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Jesus Jiménez-Barbero, Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Matthieu Sollogoub, Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorCorresponding Author
Prof. Matthieu Sollogoub
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Jesus Jiménez-Barbero, Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Matthieu Sollogoub, Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorBixue Xu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
These authors contributed equally to this work.
Search for more papers by this authorLuca Unione
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
These authors contributed equally to this work.
Search for more papers by this authorDr. Joao Sardinha
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Lisboa (Portugal)
Search for more papers by this authorShaoping Wu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorProf. Mélanie Ethève-Quelquejeu
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorProf. Amelia Pilar Rauter
Centro de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Lisboa (Portugal)
Search for more papers by this authorProf. Yves Blériot
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Université de Poitiers, UMR CNRS 7285, IC2MP, 4, avenue Michel Brunet, 86022 Poitiers Cedex (France)
Search for more papers by this authorDr. Yongmin Zhang
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorDr. Sonsoles Martín-Santamaría
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Faculty of Pharmacy, Universidad CEU San Pablo, 28668-Madrid (Spain)
Search for more papers by this authorDr. Dolores Díaz
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Search for more papers by this authorCorresponding Author
Prof. Jesus Jiménez-Barbero
Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Jesus Jiménez-Barbero, Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Matthieu Sollogoub, Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorCorresponding Author
Prof. Matthieu Sollogoub
Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Jesus Jiménez-Barbero, Chemical and Physical Biology, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid (Spain)
Matthieu Sollogoub, Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR CNRS 8232, IPCM, 4, place Jussieu, 75005 Paris (France)
Search for more papers by this authorThe group in Paris thank the China Scholarship Council for Ph.D. fellowships to B.X. and S.W., and Fundação para a Ciência e Tecnologia for a research grant (J.S.). The groups in Madrid thank COST actions BM1103 and CM1102, the MINECO grants CTQ2012-32025 and CTQ2011-22724, and the European Commission DYNANO and GLYCOPHARM ITN-projects. We also thank the CAI-NMR of University Complutense for NMR spectrometer time and CESGA (USC) for supercomputing time.
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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