A Chemical Approach to Introduce 2,6-Diaminopurine and 2-Aminoadenine Conjugates into Oligonucleotides without Need for Protecting Groups

Org Lett. 2022 Aug 26;24(33):6111-6116. doi: 10.1021/acs.orglett.2c01848. Epub 2022 Aug 16.

Abstract

We report a simple, postsynthetic strategy for synthesis of oligonucleotides containing 2,6-diaminopurine nucleotides and 2-aminoadenine conjugates using 2-fluoro-6-amino-adenosine. The strategy allows introduction of 2,6-diaminopurine and other 2-amino group-containing ligands. The strongly electronegative 2-fluoro deactivates 6-NH2 obviating the need for any protecting group on adenine, and simple aromatic nucleophilic substitution of fluorine makes reaction with aqueous NH3 or R-NH2 feasible at the 2-position.

MeSH terms

  • 2-Aminopurine* / analogs & derivatives
  • Adenine
  • Oligonucleotides*

Substances

  • Oligonucleotides
  • 2-Aminopurine
  • 2,6-diaminopurine
  • Adenine