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Flexible Alkyne-Linked Thymidine Phosphoramidites and Triphosphates for Chemical or Polymerase Synthesis and Fast Postsynthetic DNA Functionalization through Copper-Catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition.

Alessandro PanattoniRadek PohlMichal Hocek
Published in: Organic letters (2018)
Two alternative flexible alkyne-linked thymine nucleosides (propargyl-diethylene glycol- or undecyn-linked 5-hydroxymethyluracil derivatives), as well as their phosphoramidites and triphosphates, were designed and synthesized. The nucleoside 3'- O-phosphoramidites were successfully incorporated into oligonucleotides on a solid support, whereas the nucleoside triphosphates served as good substrates for polymerase synthesis of modified DNA, which underwent fast and efficient copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC) reactions.
Keyphrases
  • circulating tumor
  • cell free
  • single molecule
  • nucleic acid
  • structural basis
  • solid state
  • metal organic framework
  • circulating tumor cells