Highly efficient solid phase synthesis of oligonucleotide analogs containing phosphorodithioate linkages

Nucleic Acids Res. 2000 May 1;28(9):E40. doi: 10.1093/nar/28.9.e40.

Abstract

A triester method for the synthesis of deoxynucleoside phosphorodithioate dimers is described. The phosphorodithioate linkage is introduced using a new dithiophosphorylating reagent DPSE-SP(S)Cl(2)where DPSE = 2-diphenylmethylsilylethyl. This group is removed quickly using tetra-butylammonium fluoride leading to the quantitative formation of phosphorodithioate diesters uncontaminated with the corresponding phosphorothioates. The utility of this group is demonstrated by the synthesis of a penta-decathymidylic acid, [T(PS(2))T(PO(2))](7)T, which contains alternating phosphorodithioate/phosphate diester internucleotide linkages.

MeSH terms

  • Esters / chemistry
  • Indicators and Reagents
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligonucleotides / chemical synthesis*
  • Organothiophosphorus Compounds / chemistry
  • Phosphates / chemical synthesis*

Substances

  • 2-diphenylmethylsilylethyldithiophosphorodichloridate
  • Esters
  • Indicators and Reagents
  • Oligonucleotides
  • Organothiophosphorus Compounds
  • Phosphates
  • pentadecathymidylic acid
  • phosphorodithioic acid