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

Masayuki Takeuchi, Toshihisa Mizuno, Seiji Shinkai, Shohei Shirakami, Toshiyuki Itoh

Research output: Contribution to journalArticle

53 Citations (Scopus)

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 (Δ[θ]) 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. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3311-3322
Number of pages12
JournalTetrahedron Asymmetry
Volume11
Issue number16
DOIs
Publication statusPublished - Aug 25 2000

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Boronic Acids
monosaccharides
Monosaccharides
Chirality
carbohydrates
Dichroism
chirality
dichroism
Derivatives
acids
Acids
selectivity
galactose
Arabinose
Mannose
Galactose
Scaffolds
discrimination
ferrocene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Chirality sensing of saccharides using a boronic acid-appended chiral ferrocene derivative. / Takeuchi, Masayuki; Mizuno, Toshihisa; Shinkai, Seiji; Shirakami, Shohei; Itoh, Toshiyuki.

In: Tetrahedron Asymmetry, Vol. 11, No. 16, 25.08.2000, p. 3311-3322.

Research output: Contribution to journalArticle

Takeuchi, Masayuki ; Mizuno, Toshihisa ; Shinkai, Seiji ; Shirakami, Shohei ; Itoh, Toshiyuki. / Chirality sensing of saccharides using a boronic acid-appended chiral ferrocene derivative. In: Tetrahedron Asymmetry. 2000 ; Vol. 11, No. 16. pp. 3311-3322.
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