Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions

Org Lett. 2010 Jun 4;12(11):2496-9. doi: 10.1021/ol100676j.

Abstract

Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemistry*
  • Combinatorial Chemistry Techniques
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • RNA / chemical synthesis*
  • RNA / chemistry

Substances

  • Amidines
  • Oligonucleotides
  • RNA