Efficient cross-linking to cytidine by functional nucleobases capable of in situ activation

Nucleic Acids Symp Ser. 1999:(42):43-4. doi: 10.1093/nass/42.1.43.

Abstract

We have previously demonstrated that the ODNs with 2-amino-6-(2-phenylsulfoxyethyl)purine nucleoside derivative were capable of efficient interstrand cross-linking with cytidine selectively. In this new strategy, less reactive precursor was auto-activated within a duplex to generate 2-amino-6-vinylpurine derivative. However, it turned out that 2-amino-6-(2-phenylsulfinyl)-ethylpurine nucleoside was not applicable as the precursor for the synthesis of DNA oligomers with G-rich sequences. In this report, 2-amino-6-(2-methylsulfinylethyl)purine nucleoside has been proven to be more suitable as a precursor for DNA synthesis. In addition, the ODNs incorporating either 2-amino-6-(2-phenylsulfoxy ethyl)purine or 2-amino-6-vinylpurine showed high reactivity toward the cytidine at the target site but quite less reactivity was observed for it at non-target site, demonstrating high site-selectivity.

MeSH terms

  • Base Sequence
  • Cross-Linking Reagents
  • Cytidine / chemistry*
  • DNA / chemical synthesis*
  • DNA / chemistry
  • Indicators and Reagents
  • Oligodeoxyribonucleotides / chemical synthesis
  • Oligodeoxyribonucleotides / chemistry*
  • Purine Nucleosides*
  • Sulfoxides

Substances

  • Cross-Linking Reagents
  • Indicators and Reagents
  • Oligodeoxyribonucleotides
  • Purine Nucleosides
  • Sulfoxides
  • Cytidine
  • DNA