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Title: Boronic acid-based bipyridinium salts as tunable receptors for monosaccharides and alpha-hydroxycarboxylates. Author: Gamsey S, Miller A, Olmstead MM, Beavers CM, Hirayama LC, Pradhan S, Wessling RA, Singaram B. Journal: J Am Chem Soc; 2007 Feb 07; 129(5):1278-86. PubMed ID: 17263411. Abstract: Several novel diboronic acid-substituted bipyridinium salts were prepared and, using a fluorescent reporter dye, were tested for their ability to selectively bind various monosaccharides and alpha-hydroxycarboxylates in an aqueous medium. The fluorescence sensing mechanism relies on the formation of a ground-state charge-transfer complex between the dye and bipyridinium. An X-ray crystal structure of this complex is described herein. Glucose selectivity over fructose and galactose was achieved by designing the bipyridinium-based receptors to be capable of attaining a 1:1 receptor/substrate stoichiometry via cooperative diboronic acid binding.[Abstract] [Full Text] [Related] [New Search]