Selective binding of D2h-symmetrical, acetylene-linked pyridine/pyridone macrocycles to maltoside

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.