Stereochemical and Regiochemical Trends in the Selective Detection of Saccharides

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• 作者：Shan Jiang ; Jorge O. Escobedo ; Kyu Kwang Kim ; Onur Alptü ; rk ; George K. Samoei ; Sayo O. Fakayode ; Isiah M. Warner ; Oleksandr Rusin ; Robert M. Strongin
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：September 20, 2006
• 年：2006
• 卷：128
• 期：37
• 页码：12221 - 12228
• 全文大小：462K
• 年卷期：v.128,no.37(September 20, 2006)
• ISSN：1520-5126

文摘

Several discreet sugar-boronate complexes exist in solution. This is due to the complex equilibriabetween isomeric species of even the simplest monosaccharides. In the current investigation, we determinethe regio- and stereochemical features of the various equilibrating sugar isomers that induce signaltransduction in boronic acid chemosensors such as 1 as well as 2 and 3. We present a unique exampleof a chemosensor (1) that is selective for ribose, adenosine, nucleotides, nucleosides, and congeners. Asa result of this study, we are able to predict and achieve selective fluorescence and colorimetric responsesto specific disaccharides as a consequence of their terminal sugar residue linkage patterns andconfigurations. We also find that the combined use of chemosensors exhibiting complementary reactivitiesmay be used cooperatively to obtain enhanced selectivity for ribose and rare saccharides.