Streamlined process for the chemical synthesis of RNA using 2'-O-thionocarbamate-protected nucleoside phosphoramidites in the solid phase

J Am Chem Soc. 2011 Aug 3;133(30):11540-56. doi: 10.1021/ja201561z. Epub 2011 Jul 11.

Abstract

An improved method for the chemical synthesis of RNA was developed utilizing a streamlined method for the preparation of phosphoramidite monomers and a single-step deprotection of the resulting oligoribonucleotide product using 1,2-diamines under anhydrous conditions. The process is compatible with most standard heterobase protection and employs a 2'-O-(1,1-dioxo-1λ(6)-thiomorpholine-4-carbothioate) as a unique 2'-hydroxyl protective group. Using this approach, it was demonstrated that the chemical synthesis of RNA can be as simple and robust as the chemical synthesis of DNA.

MeSH terms

  • Molecular Structure
  • Morpholines / chemistry*
  • Nucleosides / chemistry*
  • Organophosphorus Compounds / chemistry*
  • RNA / chemical synthesis*
  • RNA / chemistry
  • Sulfur Compounds / chemistry*

Substances

  • 2'-O-(1,1-dioxo-1lamda(6)-thiomorpholine-4-carbothioate)
  • Morpholines
  • Nucleosides
  • Organophosphorus Compounds
  • Sulfur Compounds
  • phosphoramidite
  • RNA