Abstract
Abstract Podand- and crown-types of new chiral receptors, characterized by a chiral polyether skeleton and an amide junction, were derived from naturally occurring monensin ionophore. Their chiral recognition ability was investigated by ion-selective electrode and 1H-NMR spectroscopic methods. Several podand-type monensin amides formed 1:1 complexes with chiral amine salts and exhibited excellent enantiomer selectivity. Since biological monensin and its macrocyclic derivatives were less effective for chiral recognition, a molecular combination of pseudo-cyclic monensin cavity, chiral polyether skeleton and neutral amide moiety offered high enantiomer selectivity. Chemical modification of biological monensin allowed remarkable development of new ionophoric-functions and provided an effective synthetic strategy for chiral receptors.
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