Molecular recognition of mono- and disaccharides through interaction with p-iodophenylboronic acid in capillary electrophoresis with a chemiluminescence detection system.
Molecular recognition of mono- and disaccharides was performed making use of the interaction between their diol groups and p-iodophenylboronic acid in capillary electrophoresis (CE) with a chemiluminescence (CL) detection system. p-Iodophenylboronic acid acted as an enhancer for luminol-horseradish peroxidase-hydrogen peroxide CL reaction. p-Iodophenylboronic acid was injected as a sample into the present system to give a CL peak on the electropherogram. The CL intensities were examined using running buffers including mono- and disaccharides. The CL intensities with 1-methyl-D-glucoside, D-saccharose, D-maltose, D-glucose, and D-fructose decreased in this order. The decrease in CL intensity was based on the formation by p-iodophenylboronic acid of cyclic esters with mono- and disaccharides, particularly with those including cis-diol groups. That is, the decrease in CL intensity affected the specific complexation between p-iodophenylboronic acids and saccharides, leading to the molecular recognition of saccharides. We also report separation of a mixture of p-iodophenol and p-iodophenylboronic acid as well as estimation of the apparent binding constant between p-iodophenylboronic acid and saccharides taking advantage of their molecular recognition behavior.
Tsukagoshi
Kazuhiko
K
Department of Chemical Engineering and Materials Science, Faculty of Engineering, Doshisha University, Kyotanabe 610-0321, Japan. ktsukago@mail.doshisha.ac.jp
Matsumoto
Kyohei
K
Ueno
Futoshi
F
Noda
Keiichi
K
Nakajima
Riichiro
R
Araki
Koji
K
D001896:Boron Compounds / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D007462:Iodobenzenes / Q000737:chemistry*; D049449:Luminescence; D009005:Monosaccharides / Q000737:chemistry*
D001896:Boron Compounds; D004187:Disaccharides; D007462:Iodobenzenes; D009005:Monosaccharides; C080454:4-iodophenylboronic acid