Specific complexation of disaccharides with diphenyl-3,3′-diboronic acid that can be detected by circular dichroism

Kaoru Kondo, Yutaka Shiomi, Miwako Saisho, Takaaki Harada, Seiji Shinkai

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Abstract

For the development of new receptor molecules that can recognize sugar molecules, we synthesized diphenyl-3,3′-diboronic acid (2). The distance between the two boronic acids in 2 is designed so that it can selectively form cyclic 1:1 complexes with disaccharides. It was shown that 2 forms 1:1 complexes with several disaccharides and gives the characteristic exciton coupling in CD spectroscopy owing to immobilization of the two phenyl rings. Thus, the absolute configuration was successfully predicted from the sign of the exciton coupling.

Original languageEnglish
Pages (from-to)8239-8252
Number of pages14
JournalTetrahedron
Volume48
Issue number38
DOIs
Publication statusPublished - 1992
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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