Probing the Importance of Host Symmetry on Carbohydrate Recognition

Anne-Doriane Manick (1) , Chunyang Li (2) , Elise Antonetti (1) , Muriel Albalat (1) , Yoann Cotelle (1) , Paola Nava (1) , Jean-Pierre Dutasta (3) , Bastien A Chatelet (1) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 Sichuan University of Science and Engineering, Zigong
3 LC - Laboratoire de Chimie - UMR5182

The design of molecular cages with low symmetry could allow for more specific tuning of their properties and better mimic the unsymmetrical and complex environment of protein pockets. However, the added value of lowering symmetry of molecular receptors has been rarely demonstrated. Herein, C 3-and C 1-symmetrical cages, presenting the same recognition sites, have been synthesized and investigated as hosts for carbohydrate recognition. Structurally related derivatives of glucose, galactose and mannose were found to have greater affinity to the receptor with the lowest symmetry than to their C 3-symmetrical analogue. According to the host cavity modelling, the C 1 symmetry receptor exhibits a wider opening than its C 3-symmetrical counterpart, providing easier access and thus promoting guest proximity to binding sites. Moreover, our results show the high stereoand substrate selectivity of the C 1 symmetry cage with respect to its C 3 counterpart in the recognition of sugars.

Domaines: Chimie

Anne-Doriane Manick, Chunyang Li, Elise Antonetti, Muriel Albalat, Yoann Cotelle, et al.. Probing the Importance of Host Symmetry on Carbohydrate Recognition. Chemistry - A European Journal, 2023, pp.e202203212. ⟨10.1002/chem.202203212⟩. ⟨hal-03961776⟩