Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible linkage

Masahiko Inouye; Junya Chiba; Hiroyuki Nakazumi

doi:10.1021/jo9911138

Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible linkage

Masahiko Inouye^*, Junya Chiba, Hiroyuki Nakazumi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

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 hydrogenbonding site for saccharides.

Original language	English
Pages (from-to)	8170-8176
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	64
Issue number	22
DOIs	https://doi.org/10.1021/jo9911138
State	Published - 1999/10/29

ASJC Scopus subject areas

Organic Chemistry

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title = "Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible linkage",

abstract = "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 hydrogenbonding site for saccharides.",

author = "Masahiko Inouye and Junya Chiba and Hiroyuki Nakazumi",

year = "1999",

month = oct,

day = "29",

doi = "10.1021/jo9911138",

language = "英語",

volume = "64",

pages = "8170--8176",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible linkage

AU - Inouye, Masahiko

AU - Chiba, Junya

AU - Nakazumi, Hiroyuki

PY - 1999/10/29

Y1 - 1999/10/29

N2 - 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 hydrogenbonding site for saccharides.

AB - 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 hydrogenbonding site for saccharides.

UR - http://www.scopus.com/inward/record.url?scp=0033615518&partnerID=8YFLogxK

U2 - 10.1021/jo9911138

DO - 10.1021/jo9911138

M3 - 学術論文

AN - SCOPUS:0033615518

SN - 0022-3263

VL - 64

SP - 8170

EP - 8176

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Glucopyranoside recognition by polypyridine-macrocyclic receptors possessing a wide cavity with a flexible linkage

Abstract

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