Synthesis and properties of 2'-O,4'-C-ethyleneoxy bridged 5-methyluridine

Org Lett. 2013 Jul 19;15(14):3702-5. doi: 10.1021/ol401566r. Epub 2013 Jul 1.

Abstract

2'-O,4'-C-Ethyleneoxy bridged 5-methyluridine (EoNA-T), possessing a seven-membered linkage and an anomeric 4'-carbon, was synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. The EoNA-modified oligonucleotides significantly stabilized the duplexes with single-stranded RNA and triplexes with double-stranded DNA relative to the natural oligonucleotide and oligonucleotides modified by another seven-membered bridged 5-methyluridine, 2',4'-BNA(COC)-T. In addition, EoNA-T showed excellent nuclease resistance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • DNA / chemistry*
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry*
  • Oligonucleotides, Antisense / chemistry*
  • RNA / chemistry*
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis*
  • Uridine / chemistry*

Substances

  • Oligonucleotides
  • Oligonucleotides, Antisense
  • ribothymidine
  • RNA
  • DNA
  • Uridine