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- Title
Allostery in Guest Binding of Rim-to-Rim-Connected Homoditopic Biscavitands.
- Authors
Shimoyama, Daisuke; Yamada, Hitomi; Ikeda, Toshiaki; Sekiya, Ryo; Haino, Takeharu
- Abstract
Rim-to-rim-connected phosphonate biscavitands 1a and 1b were synthesized. Crystal structure analysis and variable-temperature NMR spectroscopy studies reveal that 1a is more rigid in conformation than 1b. Biscavitands 1a and 1b bind cationic guests G1- G3 through hydrogen bonding and CH-π interactions, demonstrating positive and negative allosteric effects, respectively. The allosteric effects in guest binding are associated with the conformational flexibilities of 1a and 1b. The positive allosteric effect of 1a is directed by the tightly connected cavities, in which information of the first guest binding is transferred to the remaining cavity, which becomes preorganized. In contrast, a slightly negative allosteric effect is found in more-flexible 1b.
- Subjects
CHEMICAL reactions; ORGANIC synthesis; CRYSTAL structure; CRYSTALLOGRAPHY; CATIONS
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 20, p3300
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600410