Selective Binding of D2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside
Selective Binding of D2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside
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DOI：
10.1021/jo2003055
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发表时间：
2011-05-06
影响因子：
3.6
通讯作者：
Inouye, Masahiko
中科院分区：
文献类型：
--
作者：
Abe, Hajime;Chida, Yusuke;Inouye, Masahiko
采用Cu（II）介导氧化均偶联的串联二乙基前体制备了具有吡啶-吡啶-吡啶模块的糖识别大环宿主分子。在CH2Cl2中，宿主分子与十二烷基β -麦芽糖苷（K-a = 1.4 × 10(6) M-1）的关联比与辛基单己糖(K-a =约2 × 10（3)至1 × 10(4) M-1）的关联强得多，并伴有诱导cd。研究了一种全吡啶大环宿主，其与糖的结合强度弱于吡啶-吡啶-吡啶的结合强度。
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 beta-maltoside much more strongly K-a = 1.4 x 10(6) M-1) than with octyl monohexosides (K-a = ca. 2 x 10(3) to 1 x 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.