Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine

Tony D. James, K. R.A. Samankumara Sandanayake, Ritsuko Iguchi, Seiji Shinkai

Research output: Contribution to journalArticle

396 Citations (Scopus)

Abstract

Two boronic acid systems, monoboronic acid 3 and diboronic acid 8, were synthesized. When saccharides form cyclic boronate esters with these boronic acids, the Lewis acid–base interaction between the boronic acid moiety and tertiary amine is strengthened; when saccharides form cyclic boronate esters with boronic acids the acidity of the boronic acid is enhanced. The strength of this acid–base interaction modulates the photoinduced electron transfer (PET) from the amine to anthracene. Both of these compounds show increased fluoresecence at pH 7.77 through supression of the photoinduced electron transfer from nitrogen to anthracene on saccharide binding, a direct result of the stronger boron–nitrogen bond. Compound 3 shows the typical selectivity of monoboronic acids towards saccharides. Compound 8 which has a cleftlike structure is particularly selective and sensitive for glucose due to the formation of an intramolecular 1:1 complex between the two boronic acids and the 1,2- and 4,6-hydroxyls of glucose. This is the first example in which ditopic recognition of monosaccharides is achieved in a PET sensor system.

Original languageEnglish
Pages (from-to)8982-8987
Number of pages6
JournalJournal of the American Chemical Society
Volume117
Issue number35
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

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Boronic Acids
Amines
Electrons
Acids
Sensors
Esters
Anthracene
Glucose
Monosaccharides
Acidity
Hydroxyl Radical
Nitrogen

All Science Journal Classification (ASJC) codes

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

Cite this

Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine. / James, Tony D.; Samankumara Sandanayake, K. R.A.; Iguchi, Ritsuko; Shinkai, Seiji.

In: Journal of the American Chemical Society, Vol. 117, No. 35, 01.01.1995, p. 8982-8987.

Research output: Contribution to journalArticle

James, Tony D. ; Samankumara Sandanayake, K. R.A. ; Iguchi, Ritsuko ; Shinkai, Seiji. / Novel Saccharide-Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine. In: Journal of the American Chemical Society. 1995 ; Vol. 117, No. 35. pp. 8982-8987.
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