分子识别
对称(几何)
化学
选择性
半乳糖
甘露糖
受体
双侧对称
结晶学
基质(水族馆)
立体化学
化学物理
分子
数学
生物化学
生物
几何学
有机化学
机械工程
生态学
工程类
催化作用
作者
Anne‐Doriane Manick,Chunyang Li,Élise Antonetti,Muriel Albalat,Yoann Cotelle,Paola Nava,Jean‐Pierre Dutasta,Bastien Châtelet,Alexandre Martinez
标识
DOI:10.1002/chem.202203212
摘要
Abstract 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 stereo‐ and substrate selectivity of the C 1 symmetry cage with respect to its C 3 counterpart in the recognition of sugars.
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