K. Koumoto et al., DESIGN OF A VISUALIZED SUGAR SENSING SYSTEM UTILIZING A BORONIC ACID AZOPYRIDINE INTERACTION, Supramolecular chemistry (Print), 9(3), 1998, pp. 203
The boronic acid-amine (B-N) interaction was applied to the molecular
design of a visualized sensing system for saccharides. 3-Nitrophenyl-b
oronic acid (3b) interacts with the pyridine nitrogen of 4-(4-dimethyl
aminophenyl-azo) pyridine (2) in methanol and changes its color from y
ellow to orange. Added saccharides form complexes with 3b and enhance
the acidity of the boronic acid group. As a result, the B-N interactio
n becomes stronger and the intensified intramolecular charge-transfer
band changes the solution color to red. By combined H-1-NMR and absorp
tion spectroscopic studies, four association constants governing the p
resent ternary complex system have been determined. In case of D-fruct
ose, the 3b.D-fructose complex can interact with 2240 times more stron
gly than 3b and the 2.3b complex can associate D-fructose 241 times mo
re strongly than 3b. Clearly, the B-N interaction not only enables the
colorimetric saccharide sensing but also enhances the association abi
lity (i.e., sensitivity). Thus, the present paper offers a novel basic
concept for molecular design of visualized saccharide sensing systems
.