Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside

Hajime Abe; Yusuke Chida; Hiroyuki Kurokawa; Masahiko Inouye

doi:10.1021/jo2003055

Selective binding of D_2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside

Hajime Abe^*, Yusuke Chida, Hiroyuki Kurokawa, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

26 Scopus citations

Abstract

A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH₂Cl₂, the host molecule associated with dodecyl β-maltoside much more strongly (K _a = 1.4 × 10⁶ M^-1) than with octyl monohexosides (K_a = ca. 2 × 10³ to 1 × 10 ⁴ M^-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.

Original language	English
Pages (from-to)	3366-3371
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	76
Issue number	9
DOIs	https://doi.org/10.1021/jo2003055
State	Published - 2011/05/06

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo2003055

Cite this

@article{840e3fc7f1624052bb496228173fe601,

title = "Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside",

abstract = "A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH2Cl2, the host molecule associated with dodecyl β-maltoside much more strongly (K a = 1.4 × 106 M-1) than with octyl monohexosides (Ka = ca. 2 × 103 to 1 × 10 4 M-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.",

author = "Hajime Abe and Yusuke Chida and Hiroyuki Kurokawa and Masahiko Inouye",

year = "2011",

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T1 - Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside

AU - Abe, Hajime

AU - Chida, Yusuke

AU - Kurokawa, Hiroyuki

AU - Inouye, Masahiko

PY - 2011/5/6

Y1 - 2011/5/6

N2 - A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH2Cl2, the host molecule associated with dodecyl β-maltoside much more strongly (K a = 1.4 × 106 M-1) than with octyl monohexosides (Ka = ca. 2 × 103 to 1 × 10 4 M-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.

AB - A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH2Cl2, the host molecule associated with dodecyl β-maltoside much more strongly (K a = 1.4 × 106 M-1) than with octyl monohexosides (Ka = ca. 2 × 103 to 1 × 10 4 M-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.

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U2 - 10.1021/jo2003055

DO - 10.1021/jo2003055

M3 - 学術論文

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AN - SCOPUS:79955551690

SN - 0022-3263

VL - 76

SP - 3366

EP - 3371

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9