Sugar 'chirality' sensing using a 'prochiral' salen-Co(II) complex

Toshihisa Mizuno, Masashi Yamamoto, Masayuki Takeuchi, Seiji Shinkai

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Abstract

A prochiral salen-Co(II) complex (6) bearing two boronic acid groups was synthesized. The saccharide-binding event was conveniently monitored by a circular dichroism (CD) spectral change. The exciton-coupling-type CD spectra thus obtained were compared with those of chiral salen-Co(II) complexes, (R)-4 and (R)-5. Very interestingly, monosaccharides which are selectively bound to (R)-4 and (R)-5 with P helicity generate the P helicity CD spectra in prochiral 6. This means that the two boronic acid groups in (R)-4 and (R)-5 are chirally preorganized suitable to the binding of these monosaccharides. Reflecting the short distance between the two boronic acid groups, 6 shows the very high selectivity for talose which has all OH groups arranged on the same side of the pyranose ring. These results indicate that 6 is useful for sugar 'chirality' sensing at visible wavelength region and prediction of D/L selectivity for (R)-4 and (R)-5. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6193-6198
Number of pages6
JournalTetrahedron
Volume56
Issue number34
DOIs
Publication statusPublished - Aug 18 2000

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Mizuno, T., Yamamoto, M., Takeuchi, M., & Shinkai, S. (2000). Sugar 'chirality' sensing using a 'prochiral' salen-Co(II) complex. Tetrahedron, 56(34), 6193-6198. https://doi.org/10.1016/S0040-4020(00)00578-0