Abstract
For the development of new receptor molecules that can precisely recognize sugar molecules, we synthesized a number of diboronic acids. Since one boronic acid can react with two OH groups (one diol group) to form a boronate ester, one diboronic acid can immobilize two diol units to form a sugar-containing macrocycle. The selectivity can be tuned by the relative spatial position of the two boronic acids and the complexation event can be read out by circular dichroism spectroscopy. When a boronic acid group is combined intramolecularly with an aminomethylfluorophore, the complexation event can be conveniently read out by fluorescence spectroscopy. This is a novel application of a PET (photoinduced electron transfer) sensor: the sugar-binding changes the strength of the B…N interaction, which eventually changes the fluorescence quenching efficiency of the amine. We have demonstrated using a chiral 1,1′-binaphthyl group as a fluorophore that even chiral recognition of sugars is possible. The porphyrin skeleton is shown to be useful not only as a platform to control the spatial position of boronic acids but also as a chromophore for reading-out the sugar configuration. These abundant examples support the superiority of boronic-acid-based covalent bond recognition over hydrogen-bond-based non-covalent bond recognition for sugars in water.
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Shinkai, S. (1997). Aqueous Sugar Sensing by Boronic-Acid-Based Artificial Receptors. In: Desvergne, J.P., Czarnik, A.W. (eds) Chemosensors of Ion and Molecule Recognition. NATO ASI Series, vol 492. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3973-1_4
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DOI: https://doi.org/10.1007/978-94-011-3973-1_4
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