TY - JOUR
T1 - Allosteric saccharide sensing by a phenylboronic-acids-appended 5,15-bis(triarylethynyl)porphyrin
AU - Hirata, Osamu
AU - Yamamoto, Masashi
AU - Sugiyasu, Kazunori
AU - Kubo, Yohei
AU - Ikeda, Masato
AU - Takeuchi, Masayuki
AU - Shinkai, Seiji
N1 - Funding Information:
We thank Ms. E. Okasaki and Ms. Hongyue Li at Kyushu University for HRMS measurements and 1 H NMR measurements, respectively. M.T. thanks Dr. Shun-ichi Tamaru and Prof. Fumito Tani for fruitful discussions. This work was partially supported by a Grant-in-Aid for COE Research ‘Design and Control of Advanced Molecular Assembly Systems’ from the Ministry of Education, Science and Culture, Japan (#08CE2005)
PY - 2002/1
Y1 - 2002/1
N2 - Porphyrin derivatives bearing two pairs of boronic acid groups (1) and one pair of boronic acid groups (2) were designed and synthesized to construct an allosteric saccharide-sensing system. Compound 1 has a diethynyl porphyrin rotational axis, which is expected to act as a saccharide-binding information transducer. Saccharide binding studies were conducted by UV-vis, fluorescent, and circular dichroism (CD) spectroscopies. In water-methanol 1:1 (v/v) mixed solvent, 1 can bind monosaccharides such as fucose and xylose due to an allosteric mechanism to produce 1:2 host/saccharide complexes. The processes were easily monitored by CD and fluorescent spectral changes. Binding constants K 1 and K 2 are evaluated to be 3800 and 3000 M -1 for l-fucose and 8900 and 4900 M -1 for d-xylose, and these K 1 values are significantly larger than that for 2 which binds monosaccharides according to conventional 1:1 host-guest stoichiometry. Thus, 1 behaves as a novel saccharide receptor exhibiting the positive homotropic effect.
AB - Porphyrin derivatives bearing two pairs of boronic acid groups (1) and one pair of boronic acid groups (2) were designed and synthesized to construct an allosteric saccharide-sensing system. Compound 1 has a diethynyl porphyrin rotational axis, which is expected to act as a saccharide-binding information transducer. Saccharide binding studies were conducted by UV-vis, fluorescent, and circular dichroism (CD) spectroscopies. In water-methanol 1:1 (v/v) mixed solvent, 1 can bind monosaccharides such as fucose and xylose due to an allosteric mechanism to produce 1:2 host/saccharide complexes. The processes were easily monitored by CD and fluorescent spectral changes. Binding constants K 1 and K 2 are evaluated to be 3800 and 3000 M -1 for l-fucose and 8900 and 4900 M -1 for d-xylose, and these K 1 values are significantly larger than that for 2 which binds monosaccharides according to conventional 1:1 host-guest stoichiometry. Thus, 1 behaves as a novel saccharide receptor exhibiting the positive homotropic effect.
UR - https://www.scopus.com/pages/publications/0042198672
UR - https://www.scopus.com/pages/publications/0042198672#tab=citedBy
U2 - 10.1016/S1472-7862(03)00002-9
DO - 10.1016/S1472-7862(03)00002-9
M3 - Article
AN - SCOPUS:0042198672
SN - 1472-7862
VL - 2
SP - 133
EP - 142
JO - Journal of Supramolecular Chemistry
JF - Journal of Supramolecular Chemistry
IS - 1-3
ER -