title: Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside.
abstract: A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH(2)Cl(2), the host molecule associated with dodecyl β-maltoside much more strongly (K(a) = 1.4 × 10(6) M(-1)) than with octyl monohexosides (K(a) = ca. 2 × 10(3) to 1 × 10(4) M(-1)), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan. abeh@pha.u-toyama.ac.jp
authors.forename: Hajime
authors.initials: H
authors.lastname: Abe
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Chida
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kurokawa
authors.forename: Masahiko
authors.initials: M
authors.lastname: Inouye
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011728:Pyridones / Q000737:chemistry*; D013379:Substrate Specificity
chemical_list: D005960:Glucosides; D047028:Macrocyclic Compounds; D011728:Pyridones; C040358:dodecyl maltoside; D000114:Acetylene