Allosteric saccharide sensing by a phenylboronic-acids-appended 5,15-bis(triarylethynyl)porphyrin

Osamu Hirata, Masashi Yamamoto, Kazunori Sugiyasu, Yohei Kubo, Masato Ikeda, Masayuki Takeuchi, Seiji Shinkai

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Abstract

Porphyrin derivatives bearing two pairs of boronic acid groups (1) and one pair of boronic acid groups (2) were designed and synthesized to construct an allosteric saccharide-sensing system. Compound 1 has a diethynyl porphyrin rotational axis, which is expected to act as a saccharide-binding information transducer. Saccharide binding studies were conducted by UV-vis, fluorescent, and circular dichroism (CD) spectroscopies. In water-methanol 1:1 (v/v) mixed solvent, 1 can bind monosaccharides such as fucose and xylose due to an allosteric mechanism to produce 1:2 host/saccharide complexes. The processes were easily monitored by CD and fluorescent spectral changes. Binding constants K 1 and K 2 are evaluated to be 3800 and 3000 M -1 for l-fucose and 8900 and 4900 M -1 for d-xylose, and these K 1 values are significantly larger than that for 2 which binds monosaccharides according to conventional 1:1 host-guest stoichiometry. Thus, 1 behaves as a novel saccharide receptor exhibiting the positive homotropic effect.

Original languageEnglish
Pages (from-to)133-142
Number of pages10
JournalJournal of Supramolecular Chemistry
Volume2
Issue number1-3
DOIs
Publication statusPublished - Jan 1 2002

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Hirata, O., Yamamoto, M., Sugiyasu, K., Kubo, Y., Ikeda, M., Takeuchi, M., & Shinkai, S. (2002). Allosteric saccharide sensing by a phenylboronic-acids-appended 5,15-bis(triarylethynyl)porphyrin. Journal of Supramolecular Chemistry, 2(1-3), 133-142. https://doi.org/10.1016/S1472-7862(03)00002-9