A New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH

作者：Cheng Yunfeng; Ni Nanting; Yang Wenqian; Wang Binghe^*

来源：Chemistry - A European Journal, 2010, 16(45): 13528-13538.

DOI：10.1002/chem.201000637

• boronic acids
• cyclohexanediol
• fluorescent probes
• methyl glucopyranose
• sensors

The boronic acid group is an important recognition moiety for sensor design. Herein, we report a series of isoquinolinylboronic acids that have extraordinarily high affinities for diol-containing compounds at physiological pH. In addition, 5-and 8-isoquinolinylboronic acids also showed fairly high binding affinities towards D-glucose (K(a) = 42 and 46m(-1), respectively). For the first time, weak but encouraging binding of cis-cyclohexanediol was found for these boronic acids. Such binding was coupled with significant fluorescence changes. Furthermore, 4-and 6-isoquinolinylboronic acids also showed the ability to complex methyl alpha-D-glucopyranose (K(a)=3 and 2M(-1), respectively).

• 出版日期2010