The synthesis of solid supports carrying base labile linkers to generate 3'-phosphate oligonucleotides

Bioorg Med Chem Lett. 2024 Sep 1:109:129819. doi: 10.1016/j.bmcl.2024.129819. Epub 2024 May 27.

Abstract

Oligonucleotides carrying 3'-terminal phosphates and conjugates are important tools in molecular biology and diagnostic purposes. We described the preparation of solid supports carrying the base labile linker 4-((2-hydroxyethyl)sulfonyl)benzamide for the solid-phase synthesis of 3'-phosphorylated oligonucleotides. These supports are fully compatible with the phosphoramidite chemistry yielding the desired 3'-phosphate oligonucleotides in excellent yields. The use of mild deprotection conditions allows the generation of partially protected DNA fragments.

Keywords: 3′-phosphorylation; Base labile linkers; Oligonucleotides; Solid support.

MeSH terms

  • Benzamides / chemical synthesis
  • Benzamides / chemistry
  • Molecular Structure
  • Oligonucleotides* / chemical synthesis
  • Oligonucleotides* / chemistry
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Phosphates / chemistry
  • Phosphorylation
  • Solid-Phase Synthesis Techniques*

Substances

  • Oligonucleotides
  • Phosphates
  • Benzamides
  • Organophosphorus Compounds
  • phosphoramidite