Synthesis of a 2-selenothymidine phosphoramidite and its incorporation into oligodeoxyribonucleotides

Curr Protoc Nucleic Acid Chem. 2010 Sep:Chapter 1:Unit 1.23.. doi: 10.1002/0471142700.nc0123s42.

Abstract

The detailed synthetic protocol for a 2-selenothymidine phosphoramidite and its use in preparing Se-derivatized oligonucleotides are described here. The Se-modified phosphoramidite synthesis was achieved by activating a 2-thiothymidine derivative, followed by introduction of selenium functionality. The coupling reaction yield of the 2-selenothymidine phosphoramidite during solid-phase synthesis is high (>95%), and the oligonucleotides containing the 2-selenothymidine derivatization are stable.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Oligodeoxyribonucleotides / chemistry*
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry*
  • Selenium / chemistry*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Thymidine / chemistry*

Substances

  • Oligodeoxyribonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • Selenium
  • Thymidine