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Glucopyranoside Recognition by Polypyridine-Macrocyclic Receptors Possessing a Wide Cavity with a Flexible Linkage

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journal contribution
posted on 08.10.1999, 00:00 by Masahiko Inouye, Junya Chiba, Hiroyuki Nakazumi
New polypyridine-macrocyclic receptors for glucopyranosides were designed and synthesized. The artificial receptors possess a terpyridine skeleton as a hydrogen-bonding site and a flexible polyoxyethylene chain as a bridge for the macrocyclic structure, in which the cavity of the receptors is large enough to incorporate pyranosides. The receptors showed high affinities for n-octyl β-(d)-glucopyranoside, and selective binding of the receptors was observed between epimeric pyranosides. The results obtained in this paper demonstrated versatility of the terpyridine skeleton as a hydrogen-bonding site for saccharides.