Synthesis and properties of a 2'-deoxy analogue of trans-3',4'-BNA with an S-type sugar conformation

Nucleic Acids Symp Ser (Oxf). 2007:(51):155-6. doi: 10.1093/nass/nrm078.

Abstract

We previously synthesized bridged nucleic acid (BNA) analogues possessing an S-type sugar conformation. Recently, we achieved the synthesis of a 2'-deoxy analogue of trans-3',4'-BNA. The structure of this compound was confirmed by X-ray crystallography, which indicated that its sugar ring had an S-type conformation. The hybridization ability of the 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide with DNA and RNA complements was evaluated, and it was found that 2'-deoxy-trans-3',4'-BNA showed superior hybridization ability compared with other BNA analogues with S-type sugar conformation.

MeSH terms

  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry*
  • Carbohydrate Conformation
  • DNA / chemistry
  • Nucleic Acid Hybridization
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Oligonucleotides / chemistry*
  • RNA / chemistry
  • Thymidine / analogs & derivatives*
  • Thymidine / chemical synthesis
  • Thymidine / chemistry

Substances

  • Bridged-Ring Compounds
  • Nucleosides
  • Oligonucleotides
  • RNA
  • DNA
  • Thymidine