General Approach for the Synthesis of Triazinyl Phosphoramidate Oligonucleotides via the Staudinger Reaction with the Use of 2‑Azido-4,6-dichloro-1,3,5-triazine.

ABSTRACT: Developing the new types of phosphate-modified oligonucleotides and methods for their synthesis is of great interest in nucleic acid chemistry, since such derivatives could be applied as diagnostic and therapeutic tools. In the present study, our previously reported synthesis of oligonucleotide bearing two dodecyl residues on the triazine core was expanded to a general approach of synthesis of a novel class of phosphate-modified nucleic acids, triazinyl phosphoramidate oligonucleotides (TPO). The proposed approach for obtaining TPO is based on the Staudinger reaction between highly reactive 2-azido-4,6-dichloro-1,3,5-triazine and the phosphite triester intermediate of oligonucleotide solid-phase synthesis, with the following β-elimination of 2-cyanoethyl protective group and substitution o

SUBMITTER: Zharkov TD 

PROVIDER: S-EPMC12508968 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature