D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module.
A D(3h)-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene ( 3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in (1)H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl(3), and was studied by (1)H NMR and X-ray analysis.
Graduate School of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama, Toyama 930-0194, Japan. abeh@pha.u-toyama.ac.jp
Hajime
H
Abe
Asuka
A
Horii
Shinya
S
Matsumoto
Motoo
M
Shiro
Masahiko
M
Inouye
D002241:Carbohydrates / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D002241:Carbohydrates