Saccharide Recognition by a Three-Arm-Shaped Host Having Preorganized Three-Dimensional Hydrogen-Bonding Sites

Yuki Ohishi*, Kentaro Masuda, Kazuki Kudo, Hajime Abe, Masahiko Inouye*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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 languageEnglish
Pages (from-to)785-793
Number of pages9
JournalChemistry - A European Journal
Volume27
Issue number2
DOIs
StatePublished - 2021/01/07

Keywords

  • glycosides
  • host–guest systems
  • hydrogen bonds
  • molecular recognition
  • solid–liquid extraction

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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