Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection

Nucleic Acids Res. 1989 Apr 11;17(7):2379-90. doi: 10.1093/nar/17.7.2379.

Abstract

Efficient solid-phase synthesis of a series of oligoribonucleotides of up to 20 residues is described that utilises the 9-fluorenylmethoxycarbonyl group (Fmoc) for 5'-protection and 4-methoxytetrahydropyran-4-yl (Mthp) for 2'-protection of ribonucleotide monomers and a phosphoramidite coupling procedure. The Fmoc group is removed after each coupling step by treatment with 0.1M DBU in acetonitrile. Oligoribonucleotides are isolated in 2'-protected form in good yield and shown to be readily and efficiently deprotected by mild acidic treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Cross-Linking Reagents
  • Fluorenes*
  • Molecular Sequence Data
  • Oligoribonucleotides / chemical synthesis*
  • Organophosphates
  • Organophosphorus Compounds / chemical synthesis
  • Ribonucleosides / chemical synthesis
  • Succinic Anhydrides

Substances

  • Cross-Linking Reagents
  • Fluorenes
  • Oligoribonucleotides
  • Organophosphates
  • Organophosphorus Compounds
  • Ribonucleosides
  • Succinic Anhydrides