Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties

This paper describes a convenient synthetic procedure for nucleoside mimics, 1−6, in which the 3‘,5‘-hydroxy groups of natural 2‘-deoxythymidine or 2‘-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3‘,5‘-dithiothymidine, 1, with AuI are also reported.