Abstract
Generally, cage-shaped hosts for saccharides can bind strongly to guest molecules because of the three-dimensional preorganized hydrogen-bonding sites. However, the preparation of cage molecules is often difficult because of the low yield of the macrocyclization step. Here, we report a three-arm-shaped molecule possessing pyridine-acetylene-phenol units as a new kind of host having a preorganized three-dimensional hydrogen-bonding site. This three-arm-shaped host was readily prepared compared to a cage-shaped analogue. This host associated with lipophilic glycosides to form chiral complexes, and the association constants were sufficiently high as to be comparable to those of the cage-shaped analogue. Furthermore, this host extracted native monosaccharides into a lipophilic solvent.
Original language | English |
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Pages (from-to) | 785-793 |
Number of pages | 9 |
Journal | Chemistry - A European Journal |
Volume | 27 |
Issue number | 2 |
DOIs | |
State | Published - 2021/01/07 |
Keywords
- glycosides
- host–guest systems
- hydrogen bonds
- molecular recognition
- solid–liquid extraction
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Organic Chemistry