Sugar sensing using chiral salen-Co(II) complexes

Toshihisa Mizuno, Masayuki Takeuchi, Seiji Shinkai

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Two chiral salen-Co(II) complexes, (R)-7 and (R)-8 bearing two boronic acid groups were synthesized. The saccharide-binding event was conveniently monitored by a spectral change in UV-vis absorption spectroscopy arising from saccharide-boronic acids complexation. Since the distance between the two boronic acid groups is shorter than other diboronic acid-based receptors, the saccharide selectivity is quite different from other systems: the largest association constant was observed for fructose and the next for talose. In addition, chiral recognition was achieved for certain saccharides: the largest discrimination was 2.1 observed for (R)-7 with D/L-allose. These results indicate that the salen-metal complexes provide an excellent basic skeleton for designing the chiral sugar sensing systems.

Original languageEnglish
Pages (from-to)9455-9468
Number of pages14
JournalTetrahedron
Volume55
Issue number31
DOIs
Publication statusPublished - Jul 30 1999

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Boronic Acids
Sugars
Bearings (structural)
Coordination Complexes
Fructose
Ultraviolet spectroscopy
Complexation
Absorption spectroscopy
Skeleton
Spectrum Analysis
Association reactions
Acids
disalicylaldehyde ethylenediamine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Mizuno, T., Takeuchi, M., & Shinkai, S. (1999). Sugar sensing using chiral salen-Co(II) complexes. Tetrahedron, 55(31), 9455-9468. https://doi.org/10.1016/S0040-4020(99)00519-0

Sugar sensing using chiral salen-Co(II) complexes. / Mizuno, Toshihisa; Takeuchi, Masayuki; Shinkai, Seiji.

In: Tetrahedron, Vol. 55, No. 31, 30.07.1999, p. 9455-9468.

Research output: Contribution to journalArticle

Mizuno, T, Takeuchi, M & Shinkai, S 1999, 'Sugar sensing using chiral salen-Co(II) complexes', Tetrahedron, vol. 55, no. 31, pp. 9455-9468. https://doi.org/10.1016/S0040-4020(99)00519-0
Mizuno, Toshihisa ; Takeuchi, Masayuki ; Shinkai, Seiji. / Sugar sensing using chiral salen-Co(II) complexes. In: Tetrahedron. 1999 ; Vol. 55, No. 31. pp. 9455-9468.
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