Development of a novel nucleoside analogue with S-type sugar conformation: 2′-deoxy- trans-3′,4′-bridged nucleic acids

Abstract

Two novel trans-3′,4′-bridged nucleic acid ( trans-3′,4′-BNA) monomers, one with a 3,5,8-trioxabicyclo[5.3.0]decane structure and the other with a 4,7-dioxabicyclo[4.3.0]nonane structure, were successfully synthesized from thymidine. The locked trans-fused ring structures of the nucleoside analogues were confirmed by X-ray crystallography, which also indicated that their furanose rings had a typical S-type conformation involving C 2′- endo or C 3′- exo sugar puckering, respectively, and the same ring conformation as that observed in the B-type helical structure of the DNA duplex.