Abstract
A cyanine dye (4) bearing two boronic acids was designed and synthesized, expecting the selective binding of monosaccharides through the formation of 1:1 intramolecular complexes. While it aggregates in water, it exists discretely in water/methanol 1:1 mixed solvent. In the latter solvent the fluorescence spectra were scarcely affected by the medium pH but efficiently increased when it formed intramolecular 1:1 complexes with monosaccharides. This complexation mode was also corroborated by CD spectroscopy and continuous variation plots. Hence, the saccharide-induced fluorescence increase is rationalized in terms of 'rigidification' of the cyanine skeleton. The association constants (K) were estimated from plots of saccharide concentration vs. fluorescence intensity: the largest K was observed for D-fructose (1.3 x 105 M-1) and the next for D-arabinose (1.0 x 104 M-1). This is a novel system for sensitive and selective fluorescence detection of monosaccharides.
Original language | English |
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Pages (from-to) | 1195-1204 |
Number of pages | 10 |
Journal | Tetrahedron |
Volume | 52 |
Issue number | 4 |
DOIs | |
Publication status | Published - Jan 1 1996 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry