O6-(Benzotriazol-1-yl)inosine Derivatives: Easily Synthesized, Reactive Nucleosides

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed

Suyeal Bae

2007

Scholarcy highlights

  • In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed
  • A novel class of O6-(benzotriazol-1-yl)inosine as well as the corresponding 2‘-deoxy derivatives can be conveniently prepared by a reaction between sugar-protected or -unprotected inosine or 2‘-deoxyinosine nucleosides and 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate
  • The reaction appears to proceed via a nucleoside phosphonium salt, and in the absence of any additional nucleophile, the released 1-hydroxybenzotriazole undergoes reaction with the formed phosphonium salt leading to the requisite O6-(benzotriazol-1-yl)inosine or 2‘-deoxyinosine derivatives
  • A fully protected DNA building block, the O6-(benzotriazol-1-yl)-2‘-deoxyinosine 5‘-O-DMT 3‘-O-phosphoramidite, has been prepared and a preliminary evaluation of its use for DNA modification has been performed. Results from these studies indicate several important facts: A single, simple methodological approach provides a class of stable, isolable ribo and 2‘-deoxyribonucleoside derivatives that possess excellent reactivity for SNAr chemistry with a wide range of nucleophiles
  • A benzotriazolyl nucleoside phosphoramidite appears to be a suitable reagent for incorporation into DNA for purposes of site-specific DNA modification
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