Synthesis of Oligobipyridine Strands Bearing Nucleoside and Amino Acid Side Chains

Abstract

The synthesis is reported of derivatives of 6,6'-dimethyl-2,2'-bipyridine in which adenosine, thymidine aid tryptophan substituents are introduced at the 4,4'-positions as amide derivatives. Artificial oligonucleoside strands derived from the corresponding trisbipyridyl ligand , in which three bipyridyl ligands are separated by methyleneoxy bridges, have been prepared. The solubility of the nucleoside-substituted ligands in organic solvents is poor, but acylation of the ribose or deoxyribose units present in the ligands provides a mechanism whereby organic solubility can be improved. These ligands may be used for the preparation of metallo-exoreceptors , with the potential for recognition of biological targets such as nucleic acids. Preliminary metal ion complexation studies have been carried out.