Mono- and oligosaccharide sensing by phenylboronic acid-appended 5,15-bis(diarylethynyl)porphyrin complexes

Osamu Hirata, Yohei Kubo, Masayuki Takeuchi, Seiji Shinkai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Porphyrin derivatives bearing a pair of boronic acid groups (1, 1·Zn, and 1·Cu) were designed and synthesized from 2 to construct a saccharide sensing system. Compounds 1, 1·Zn, and 1·Cu have a diethynyl porphyrin rotational axis, which is expected to act as a saccharide-binding modulator. Saccharide binding studies were conducted by UV-vis, fluorescence, and circular dichroism (CD) spectroscopies. In a water-methanol 1:1 (v/v) mixed solvent, we have found that 1·Zn can bind mono- and oligosaccharides including Lewis oligosaccharides to produce 1:1 host-saccharide complexes with the association constants of 10 2-10 3 M -1 range. This paper thus demonstrates a new principle to design a boronic acid-based saccharide receptor. Graphical Abstract.

Original languageEnglish
Pages (from-to)11211-11218
Number of pages8
JournalTetrahedron
Volume60
Issue number49
DOIs
Publication statusPublished - Nov 29 2004

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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