Highly efficient recognition of native TpT by artificial ditopic hydrogen-bonding receptors possessing a conformationally well-defined linkage

Abstract

Synthesis and binding affinity of rationally designed artificial ditopic nucleobase receptors are reported. The ditopic receptors were designed to recognize thymine-thymine dinucleotides by their two hydrogen-bonding moieties, which are connected to conformationally well-defined linkages such as ferrocene and biphenylene. The ditopic receptors exhibited a remarkably strong binding affinity for lipophilic TpT analogue in CDCl(3)/DMSO-d(6) (85:15, v/v). The binding affinity of the ditopic receptors for the dinucleotide was so high that even native TpT was extracted by them into CDCl(3). Detailed comparisons for the recognition abilities of the ditopic receptors were also conducted.