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

Albert Meyer (1) , Camille Bouillon (1) , Sébastien Vidal (2) , Jean-Jacques Vasseur (1) , François Morvan (1)

1 COBS - Chimie organique biomoléculaire de synthèse
2 MSMB - Méthodologie de synthèse et molécules bioactives

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.

Mots clés: 5′-Phosphorylated oligonucleotides; New phosphorylating reagent; 5′-Thiophosphorylated oligonucleotides; 5′-Phosphoramidate oligonucleotide; 1; 3-Dipolar cycloaddition; Click chemistry

Domaines: Chimie organique

Albert Meyer, Camille Bouillon, Sébastien Vidal, Jean-Jacques Vasseur, François Morvan. A versatile reagent for the synthesis of 5'-phosphorylated, 5'-thiophosphorylated or 5'-phosphoramidate-conjugated oligonucleotides. Tetrahedron Letters, 2006, 47 (50), pp.8867-8871. ⟨10.1016/j.tetlet.2006.10.049⟩. ⟨hal-00160263⟩