Specific complexation of saccharides with dimeric phenylboronic acid that can be detected by circular dichroism
- 1 June 1993
- journal article
- research article
- Published by Taylor & Francis in Supramolecular Chemistry
- Vol. 2 (1) , 11-17
- https://doi.org/10.1080/10610279308027501
Abstract
For the development of new receptor molecules that can recognize sugar molecules, we synthesized 2,2′-dimethoxydiphenylmethane-5,5′-diboronic acid (1) and diphenyl-3,3′-diboronic acid (2). It was shown that in the presence of 1, some mono- and disaccharides result in a CD band at 275 nm. It was also 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. The results indicate that the CD spectroscopic method using 1 or 2 as receptor molecules serves as a new sensory system for sugar molecules, and the absolute configuration of disaccharides was successfully predicted from the sign of the exciton coupling of the CD spectrum by using 2.Keywords
This publication has 16 references indexed in Scilit:
- Molecular recognition of mono- and di-saccharides by phenylboronic acids in solvent extraction and as a monolayerJournal of the Chemical Society, Chemical Communications, 1991
- Fischer route to pyrido[3,2-g]indoles. A novel receptor for urea derivativesJournal of the American Chemical Society, 1990
- 1,3-Bis(m-nitrophenyl)urea: an exceptionally good complexing agent for proton acceptorsJournal of the American Chemical Society, 1988
- Hexagonal lattice hosts for urea. A new series of designed heterocyclic receptorsJournal of the American Chemical Society, 1988
- Polar host-guest interaction. Binding of nonionic polar compounds with a resorcinol-aldehyde cyclooligomer as a lipophilic polar hostJournal of the American Chemical Society, 1988
- Enantioselective complexation of bilirubin with cyclodextrins and non-cyclic oligosaccharidesJournal of the Chemical Society, Chemical Communications, 1988
- Induced fit in synthetic receptors: nucleotide base recognition by a molecular hingeJournal of the American Chemical Society, 1987
- Free energy increments for hydrogen bonds in nucleic acid base pairsJournal of the American Chemical Society, 1987
- Convergent functional groups: synthetic and structural studiesJournal of the American Chemical Society, 1985
- Exciton chirality method and its application to configurational and conformational studies of natural productsAccounts of Chemical Research, 1972