First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism

A. Sugasaki, K. Sugiyasu, M. Ikeda, M. Takeuchi, S. Shinkai

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

We have designed phenylboronic acid group appended Ce(IV) bis(porphyrinate) double decker 1 and meso - meso linked porphyrin 2, useful for the allosteric binding of biologically important saccharides, Lewis oligosaccharides. Compound 1 binds Lewis oligosaccharides in aqueous media because of the boronic acid-diol interaction, but the complexation event can occur only above the critical concentrations because of the sigmoidal [oligosaccharide] versus [complex] isotherm. Compound 1 has a sufficiently high affinity with Lewis oligosaccharides (K = 105-106 M-2) with Hill coefficients n of 1.8-2.0, and LewisX series and Lewisa series give opposite, symmetrical CD spectra. This is the first example of efficient binding of Lewis oligosaccharides to the artificial receptor, which has become possible by positive homotropic allosterism.

Original languageEnglish
Pages (from-to)10239-10244
Number of pages6
JournalJournal of the American Chemical Society
Volume123
Issue number42
DOIs
Publication statusPublished - Oct 24 2001

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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