Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar Acids

✍ Scribed by Jianzhang Zhao; Thomas M. Fyles; Tony D. James

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 144 KB
• Volume: 116
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200454033

✦ Synopsis

The chemistry of saccharides is of paramount importance to a wealth of biological functions within nature. By providing the building blocks for processes ranging from the production of metabolic energy to tissue recognition, saccharides have found themselves to be the focus of a vast body of research aimed at understanding and mimicking their specific role and function at a cellular level. [1] Unsurprisingly the ability to derive synthetic receptors with the capacity to selectively detect specific saccharides (and related molecules) and signal their presence by altering the optical signature has captured the attention of supramolecular chemists. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Binol is an important chiral building block and has been widely used in asymmetric catalysis, [17,18] and for enantioselective fluorescence sensors bearing a variety of recognition elements. [19][20][21][22][23][24][25][26][27][28][29][30] In early work, a binol-based bisboronic acid (1) was used to recognize the enantiomers of monosaccharides, such as d/l-glucose, -fructose, and -galactose. [2,14,15] Recently