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A new class of fluorescent boronic acids that have extraordinarily high affinities for diols in aqueous solution at physiological pH.

ABSTRACT: 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 46 M(-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 ?-D-glucopyranose (K(a)=3 and 2 M(-1), respectively).

SUBMITTER: Cheng Y

PROVIDER: S-EPMC3545481 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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A new class of fluorescent boronic acids that have extraordinarily high affinities for diols in aqueous solution at physiological pH.

Cheng Yunfeng Y Ni Nanting N Yang Wenqian W Wang Binghe B

Chemistry (Weinheim an der Bergstrasse, Germany) 20101201 45

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 46 M(-1), respectively). For the first time, weak but encouraging binding of cis-cyclohexanediol was found for these boronic acids. Such binding was c ...[more]

PMID: 20938931

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