Saccharide Recognition by a Three-Arm-Shaped Host Having Preorganized Three-Dimensional Hydrogen-Bonding Sites |
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Authors: | Dr Yuki Ohishi Kentaro Masuda Kazuki Kudo Prof Dr Hajime Abe Prof Dr Masahiko Inouye |
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Institution: | 1. Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194 Japan;2. Faculty of Pharmaceutical Sciences, Himeji Dokkyo University, Kami-ohno 7-2-1, Himeji, Hyogo, 670-8524 Japan |
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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. |
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Keywords: | glycosides host–guest systems hydrogen bonds molecular recognition solid–liquid extraction |
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