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A versatile reagent for the synthesis of 5'-phosphorylated, 5'-thiophosphorylated or 5'-phosphoramidate-conjugated oligonucleotides
Journal article   Peer reviewed

A versatile reagent for the synthesis of 5'-phosphorylated, 5'-thiophosphorylated or 5'-phosphoramidate-conjugated oligonucleotides

Albert Meyer, Camille Bouillon, Sébastien Vidal, Jean-Jacques Vasseur and François Morvan
Tetrahedron Letters, Vol.47(50)
12/2006

Abstract

5′-Phosphorylated oligonucleotides New phosphorylating reagent 5′-Thiophosphorylated oligonucleotides 5′-Phosphoramidate oligonucleotide 1 3-Dipolar cycloaddition Click chemistry
We report the synthesis of a new phosphorylating reagent that is easily accessible and allows not only the chemical synthesis of 5′-phosphorylated and 5′-thiophosphorylated oligonucleotides but also the 5′-conjugation through a phosphoramidate linkage. 5′-Amino-linker and 5′-alkyne oligonucleotides were obtained and the latter was conjugated by a 1,3-dipolar cycloaddition (click chemistry) with a galactosylated azide derivative to afford 5′-galactosyl oligonucleotide with high efficiency.
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