TY - JOUR
T1 - Mono- and oligosaccharide sensing by phenylboronic acid-appended 5,15-bis(diarylethynyl)porphyrin complexes
AU - Hirata, Osamu
AU - Kubo, Yohei
AU - Takeuchi, Masayuki
AU - Shinkai, Seiji
N1 - Funding Information:
We thank Ms. Hongyue Li at Kyushu University for 1 H NMR measurements. The present work is partially supported by a Grant-in-Aid for the 21st Century COE Program, ‘Functional Innovation of Molecular Informatics’ from the Ministry of Education, Culture, Science, Sports and Technology of Japan.
PY - 2004/11/29
Y1 - 2004/11/29
N2 - 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 10 2-10 3 M -1 range. This paper thus demonstrates a new principle to design a boronic acid-based saccharide receptor. Graphical Abstract.
AB - 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 10 2-10 3 M -1 range. This paper thus demonstrates a new principle to design a boronic acid-based saccharide receptor. Graphical Abstract.
KW - Saccharide sensing
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U2 - 10.1016/j.tet.2004.08.061
DO - 10.1016/j.tet.2004.08.061
M3 - Article
AN - SCOPUS:7044260890
SN - 0040-4020
VL - 60
SP - 11211
EP - 11218
JO - Tetrahedron
JF - Tetrahedron
IS - 49
ER -