Chirality sensing of saccharides using a boronic acid-appended chiral ferrocene derivative

被引:50
作者
Takeuchi, M
Mizuno, T
Shinkai, S [1 ]
Shirakami, S
Itoh, T
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Biochem & Chem, Fukuoka 8128581, Japan
[2] Okayama Univ, Fac Educ, Grad Sch Nat Sci & Technol, Okayama 7008530, Japan
[3] Okayama Univ, Fac Educ, Dept Chem, Okayama 7008530, Japan
关键词
D O I
10.1016/S0957-4166(00)00307-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 (Delta[theta]) 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 (K-D and K-L, respectively) were determined: among them, (R)-9 showed a significant discrimination ability for mannose (K-L/K-D = 2.6) and arabinose (K-L/K-D = 1/2.4). The origin of D/L selectivity was discussed on the basis of computational studies on (R)-9 saccharide complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3311 / 3322
页数:12
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