Enhancing Effect of Phenylboronic Acid Compounds and Their Interactions with the Diol Groups of Saccharides in a Capillary Electrophoresis-Chemiluminescence Detection System
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In our previous study, we proposed molecular recognition of mono- and disaccharides making use of the interaction between their diol groups and <i>p</i>-iodophenylboronic acid in capillary electrophoresis with a chemiluminescence detection system. Here, to extend our knowledge of molecular recognition, we first examined the enhancing effects of four phenylboronic acid compounds other than <i>p</i>-iodophenylboronic acid <i>i.e.</i>, 4-biphenylboronic acid, 4-octyloxyphenyl-boronic acid, 3-octyloxyphenylboronic acid, and 4-dodecyloxyphenylboronic acid, for luminol-hydrogen peroxide-horseradish peroxidase reaction in the capillary electrophoresis-chemiluminescence detection system. Only 4-biphenylboronic acid showed an enhancing effect similar to that of <i>p</i>-iodophenylboronic acid; the effect was determined over the range of 0.5 - 10 µM in this system. Second, we estimated the apparent stability constants between the diol groups of saccharides (1-methyl-<font size=-2>D</font>-glucoside, <font size=-2>D</font>-saccharose, and <font size=-2>D</font>-fructose) and the boronic acid moieties of the two enhancers, <i>p</i>-iodophenylboronic acid and 4-biphenylboronic acid. The apparent binding constants obtained here provided insight to confirm the principle of molecular recognition for the saccharides examined here.
- Analytical Sciences
Analytical Sciences 23(2), 227-230, 2007-02-10
The Japan Society for Analytical Chemistry