Mono- and oligosaccharide sensing by phenylboronic acid-appended 5,15-bis(diarylethynyl)porphyrin complexes |
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Authors: | Osamu Hirata Seiji Shinkai |
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Institution: | Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan |
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Abstract: | Porphyrin derivatives bearing a pair of boronic acid groups (1, 1·Zn, and 1·Cu) were designed and synthesized from 2 to construct a saccharide sensing system. Compounds 1, 1·Zn, and 1·Cu have a diethynyl porphyrin rotational axis, which is expected to act as a saccharide-binding modulator. Saccharide binding studies were conducted by UV-vis, fluorescence, and circular dichroism (CD) spectroscopies. In a water-methanol 1:1 (v/v) mixed solvent, we have found that 1·Zn can bind mono- and oligosaccharides including Lewis oligosaccharides to produce 1:1 host-saccharide complexes with the association constants of 102−103 M−1 range. This paper thus demonstrates a new principle to design a boronic acid-based saccharide receptor. |
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Keywords: | Saccharide sensing |
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