Chirality sensing of saccharides using a boronic acid-appended chiral ferrocene derivative |
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| Institution: | 1. Department of Applied Chemistry, Graduate School of Engineering, University of Hyogo, Himeji, Hyogo 671-2201, Japan;2. Graduate School of Material Science, University of Hyogo, 3-2-1, Kouto, Kamigori, Ako, Hyogo 678-1297, Japan;3. Synchrotron Radiation Nanotechnology Center, University of Hyogo, 1-490-2, Kouto, Shingu, Tatsuno, Hyogo 679-5165, Japan;4. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan;5. SPring-8 Service Co., Ltd., 1-20-5, Kouto, Shingu, Tatsuno, Hyogo 679-5165, Japan;1. ENSCM – AM2N, UMR 5253 – Institut Charles Gerhardt, Montpellier Cedex, France;2. PSL Research University, Chimie ParisTech – CNRS, Institut de Recherche de Chimie Paris, Paris, France |
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| Abstract: | A diboronic acid-appended chiral ferrocene derivative (R)-9 was designed and synthesized. This chiral ferrocene scaffold was obtained by resolution of the diastereomer with a monosaccharide derivative. One can therefore expect that (R)-9 would show d/l selectivity for specific monosaccharides. The complex formation of (R)-9 with various saccharides using the two boronic acid functions was conveniently monitored by a change in the circular dichroism (CD) spectra. The CD spectral change (Δθ]) induced by added monosaccharides was chiroselective: in particular, d/l-alloses and d/l-galactoses induced the 8.0- and 7.0-fold difference in the magnitude of the CD spectral change. The association constants for d- and l-saccharides (KD and KL, respectively) were determined: among them, (R)-9 showed a significant discrimination ability for mannose (KL/KD=2.6) and arabinose (KL/KD=1/2.4). The origin of d/l selectivity was discussed on the basis of computational studies on (R)-9·saccharide complexes. |
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