Binding studies of adamantanecarboxylic acid and a naphthyl-bound beta-cyclodextrin by variable temperature H-1 NMR
Binding studies of adamantanecarboxylic acid and a naphthyl-bound beta-cyclodextrin by variable temperature H-1 NMR
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DOI：
10.1021/jo9613794
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发表时间：
1996-11-15
影响因子：
3.6
通讯作者：
GarciaGaribay, MA
中科院分区：
文献类型：
--
作者：
McAlpine, SR;GarciaGaribay, MA
附着在环糊精上的发色团可能有助于监测环糊精和外部客体之间的结合状态，最近的努力致力于开发能够充当分子传感器的化合物。 1-9 预计对外部客体的敏感性应取决于客体和探针之间的相互作用，以及它们是否可以共享主体的疏水空腔或必须竞争它。我们最近表明，连接在 β-环糊精（化合物 1，方案 1）3-羟基位置上的短链萘基表现出温度依赖性的内外异构现象，能够改变其结合和传感能力。 10 在本文中，我们报告了使用 1 和 1-金刚烷甲酸 (AdCA) 11-14 进行的变温 1H NMR 研究，该研究支持与最近通过 2-(对甲苯胺)-6-萘磺酸盐 (TNS) 荧光测量提出的结合方案（方案 1）类似的结合方案。 10
Chromophores attached to cyclodextrins may help monitor the state of binding between cyclodextrin and external guests, and recent efforts have been directed to the development of compounds capable of acting as molecular sensors. 1-9 It is expected that sensitivity to external guests should depend on the interaction between the guest and the probe and on whether they may share the hydrophobic cavity of the host or they must compete for it. We recently showed that a short-tethered naphthyl group attached at the 3-hydroxy position of β-cyclodextrin (compound 1, Scheme 1) displays a temperature-dependent inside-outside isomerism that is capable of modifying its binding and sensing capabilities. 10 In this paper, we report a variable temperature 1H NMR study with 1 and 1-adamantanecarboxylic acid (AdCA) 11-14 that supports a binding scheme (Scheme 1) similar to that recently proposed from fluorescence measurements with 2-(p-toluidino)-6-naphthalenesulfonate (TNS). 10