Enhancing effect of phenylboronic acid compounds and their interactions with the diol groups of saccharides in a capillary electrophoresis-chemiluminescence detection system.
In our previous study, we proposed molecular recognition of mono- and disaccharides making use of the interaction between their diol groups and p-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 p-iodophenylboronic acid i.e., 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 p-iodophenylboronic acid; the effect was determined over the range of 0.5-10 microM in this system. Second, we estimated the apparent stability constants between the diol groups of saccharides (1-methyl-D-glucoside, D-saccharose, and D-fructose) and the boronic acid moieties of the two enhancers, p-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.
Tsukagoshi
Kazuhiko
K
Department of Chemical Engineering and Materials Science, Faculty of Engineering, Doshisha University, Kyotanabe, Japan. ktsukago@mail.doshisha.ac.jp
Ueno
Futoshi
F
Nakajima
Riichiro
R
Araki
Koji
K
D000438:Alcohols / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D006735:Horseradish Peroxidase / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D008163:Luminescent Measurements / Q000379:methods*; D008165:Luminol / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*
D000438:Alcohols; D001896:Boron Compounds; D001897:Boronic Acids; D004187:Disaccharides; D007462:Iodobenzenes; D009005:Monosaccharides; C103283:1,1'-biphenyl-4-yl-boronic acid; C080454:4-iodophenylboronic acid; D008165:Luminol; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase