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 |
|---|---|
| Pages (from-to) | 1195-1204 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 52 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Jan 1 1996 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe. / Takeuchi, Masayuki; Mizuno, Toshihisa; Shinmori, Hideyuki; Nakashima, Michio; Shinkai, Seiji.
In: Tetrahedron, Vol. 52, No. 4, 01.01.1996, p. 1195-1204.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe
AU - Takeuchi, Masayuki
AU - Mizuno, Toshihisa
AU - Shinmori, Hideyuki
AU - Nakashima, Michio
AU - Shinkai, Seiji
PY - 1996/1/1
Y1 - 1996/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0030051839&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030051839&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(95)00979-5
DO - 10.1016/0040-4020(95)00979-5
M3 - Article
AN - SCOPUS:0030051839
VL - 52
SP - 1195
EP - 1204
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 4
ER -