TY - JOUR
T1 - Circular dichroism readout of sugar recognition in the cleft of a fused-pyridine receptor
AU - Tamaru, Shun Ichi
AU - Shinkai, Seiji
AU - Khasanov, Alisher B.
AU - Bell, Thomas W.
PY - 2002/4/16
Y1 - 2002/4/16
N2 - Dicarboxamide host 2 forms 1:1 complexes with n-octyl pyranosides derived from D-glucose, D-mannose, D-galactose, D-fucose, D-lyxose, and D-arabinose. Association constants (Ka) in the range of 77-940 M-1 were measured in chloroform by means of induced circular dichroism and fluorescence spectroscopy. Variations in Ka values correspond qualitatively to expected differences in hydrogen-bonding abilities of guest hydroxyl groups. Induced circular dichroism effects for complexes of saccharides bearing equatorial 3-OH, 4-OH, and 6-OH groups show that the host chromophore is twisted in a P-helical conformation. A structural model is proposed that is also consistent with the results of previous studies involving complexation of dicarboxylic acid 1 with cationic saccharides in methanol.
AB - Dicarboxamide host 2 forms 1:1 complexes with n-octyl pyranosides derived from D-glucose, D-mannose, D-galactose, D-fucose, D-lyxose, and D-arabinose. Association constants (Ka) in the range of 77-940 M-1 were measured in chloroform by means of induced circular dichroism and fluorescence spectroscopy. Variations in Ka values correspond qualitatively to expected differences in hydrogen-bonding abilities of guest hydroxyl groups. Induced circular dichroism effects for complexes of saccharides bearing equatorial 3-OH, 4-OH, and 6-OH groups show that the host chromophore is twisted in a P-helical conformation. A structural model is proposed that is also consistent with the results of previous studies involving complexation of dicarboxylic acid 1 with cationic saccharides in methanol.
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U2 - 10.1073/pnas.082638599
DO - 10.1073/pnas.082638599
M3 - Article
C2 - 11959949
AN - SCOPUS:0037117515
SN - 0027-8424
VL - 99
SP - 4972
EP - 4976
JO - Proceedings of the National Academy of Sciences of the United States of America
JF - Proceedings of the National Academy of Sciences of the United States of America
IS - 8
ER -