Synthesis and structural studies of S-type/N-type-locked/frozen nucleoside analogues and their incorporation in RNA-selective, nuclease resistant 2'-5' linked oligonucleotides

Org Biomol Chem. 2013 Feb 7;11(5):746-57. doi: 10.1039/c2ob26762d. Epub 2012 Dec 6.

Abstract

2'-endo locked or frozen (S-type)/3'-endo locked or frozen (N-type) nucleoside analogues were synthesized. Conformational analysis based on (3)J(HH) and NOE measurements is presented which is further confirmed by X-ray crystal structural studies. 2'-5'isoDNA oligonucleotides (ON) were synthesized using these modified nucleoside analogues and UV-T(m) studies of the resultant 2'-5'isoDNA : RNA duplexes reflect the site- and sequence-dependent effects and confirm that the S-type sugar conformations were preferred over the N-type sugar geometry in such duplexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Base Sequence
  • Crystallography, X-Ray
  • DNA / chemical synthesis
  • DNA / chemistry
  • DNA / metabolism
  • Models, Molecular
  • Molecular Conformation
  • Nucleic Acid Conformation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / metabolism
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Oligonucleotides / metabolism
  • RNA / chemical synthesis
  • RNA / chemistry*
  • RNA / metabolism
  • RNA Stability
  • Ribonucleases / metabolism
  • Snakes / metabolism

Substances

  • Nucleosides
  • Oligonucleotides
  • locked nucleic acid
  • RNA
  • DNA
  • Ribonucleases