Jiang Shan, Escobedo Jorge O, Kim Kyu Kwang, Alptürk Onur, Samoei George K, Fakayode Sayo O, Warner Isiah M, Rusin Oleksandr, Strongin Robert M
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
J Am Chem Soc. 2006 Sep 20;128(37):12221-8. doi: 10.1021/ja063651p.
Several discreet sugar-boronate complexes exist in solution. This is due to the complex equilibria between isomeric species of even the simplest monosaccharides. In the current investigation, we determine the regio- and stereochemical features of the various equilibrating sugar isomers that induce signal transduction in boronic acid chemosensors such as 1 as well as 2 and 3. We present a unique example of a chemosensor (1) that is selective for ribose, adenosine, nucleotides, nucleosides, and congeners. As a result of this study, we are able to predict and achieve selective fluorescence and colorimetric responses to specific disaccharides as a consequence of their terminal sugar residue linkage patterns and configurations. We also find that the combined use of chemosensors exhibiting complementary reactivities may be used cooperatively to obtain enhanced selectivity for ribose and rare saccharides.
溶液中存在几种离散的糖 - 硼酸酯配合物。这是由于即使是最简单的单糖的异构体之间也存在复杂的平衡。在当前的研究中，我们确定了各种处于平衡状态的糖异构体的区域和立体化学特征，这些异构体在硼酸化学传感器（如1以及2和3）中诱导信号转导。我们展示了一种对核糖、腺苷、核苷酸、核苷及其类似物具有选择性的化学传感器（1）的独特示例。作为这项研究的结果，由于特定二糖的末端糖残基连接模式和构型，我们能够预测并实现对它们的选择性荧光和比色响应。我们还发现，具有互补反应性的化学传感器联合使用可以协同作用，以提高对核糖和稀有糖类的选择性。
