Direct and practical synthesis of 2′-O,4′-C-aminomethylene-bridged nucleic acid purine derivatives by transglycosylation

Abstract

Purine nucleosides of 2′-O,4′-C-aminomethylene-bridged nucleic acid (BNANC) have been directly synthesized from pyrimidine BNANC using transglycosylation reaction with high stereoselectivity and excellent yield. The BNANC purine nucleosides (adenosine, guanosine, and inosine) prepared by the direct and practical procedure were derivatized to the corresponding phosphoramidites and were incorporated into DNA. A thermal denaturation study showed that BNANC-containing oligonucleotides hybridized to RNA selectively with excellent mismatch discrimination.