Solid phase synthesis of nucleobase and ribose modified inosine nucleoside analogues

Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1649-52. doi: 10.1080/15257770701506608.

Abstract

The synthesis and the use of new N-1-dinitrophenyl-inosine based solid support is reported. The support, which binds the nucleoside by a 5'-O-monomethoxytrityl function, reacting with N-nucleophiles allowed the synthesis of a small library of N-1 alkylated inosine and AICAR derivatives. Moreover, the obtained supports, after the cleavage of the 2' -3' ribose bond, furnished a set of new N-1 alkylated-2' -3' -secoinosine derivatives in high yields.

MeSH terms

  • Aminoimidazole Carboxamide / analogs & derivatives
  • Aminoimidazole Carboxamide / chemistry
  • Inosine / analogs & derivatives*
  • Inosine / chemistry
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Ribonucleotides / chemistry
  • Ribose / chemistry*

Substances

  • N-1-dinitrophenyl-inosine
  • Nucleosides
  • Ribonucleotides
  • Aminoimidazole Carboxamide
  • Inosine
  • Ribose
  • AICA ribonucleotide