抄録
We developed a pyridine–acetylene–phenol macrocycle in which a fluorine atom was introduced in place of a hydroxy group, as a host for the selective binding to epimers of glucose. The fluorine atom was expected to work as a negatively charged infill repelling oxygen atoms of saccharides and prevent the efficient formation of a hydrogen-bond network with a glucoside, whose cross-section size is larger than those of the corresponding epimers, especially of a mannoside. UV–Vis and fluorescence titration experiments revealed that this host showed a higher affinity for a mannoside than a glucoside. 1H NMR and molecular modeling suggested that the fluorine atom acts as a moderate infill weakening the binding to a glucoside. This result indicates that selectivity for guest molecules can be modified by replacing a hydroxy group and a hydrogen atom in host molecules with a fluorine atom.
本文言語 | 英語 |
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論文番号 | e202400758 |
ジャーナル | European Journal of Organic Chemistry |
巻 | 27 |
号 | 45 |
DOI | |
出版ステータス | 出版済み - 2024/12/02 |
ASJC Scopus 主題領域
- 物理化学および理論化学
- 有機化学