Improved phosphoramidite building blocks for the synthesis of the simplified nucleic acid GNA

J Org Chem. 2009 Jun 19;74(12):4615-8. doi: 10.1021/jo900365a.

Abstract

An improved synthesis of glycol nucleic acids is reported using new phosphoramidite building blocks in which the exocyclic amino groups of adenine and guanine are protected as N-dimethylformamidines, whereas the amino group of cytosine is protected via an acetamide. Besides a more rapid synthesis with higher yields, these phosphoramidites allow the use of a quicker deprotection procedure in the subsequent solid-phase synthesis of GNA oligonucleotides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / chemistry
  • Formamides / chemistry
  • Glycols / chemical synthesis*
  • Guanine / chemistry
  • Nucleic Acids / chemical synthesis*
  • Oligonucleotides / chemical synthesis
  • Organophosphorus Compounds / chemistry*

Substances

  • Formamides
  • Glycols
  • Nucleic Acids
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • Guanine
  • Adenine