Synthesis of Phosphorodiamidate Oligonucleotide Dimers

Autor: Jennifer Albaneze-Walker, Gregor Urbanietz, Andras Horvath, Stefano Lancianesi, Alejandro Gimenez Molina, Thomas De Vijlder, Mattijs Baeten, Martine Canters
Rok vydání: 2022
Předmět:
Zdroj: The Journal of organic chemistry. 87(19)
ISSN: 1520-6904
Popis: Azido nucleosides couple with phosphoramidites via an initial iminophosphorane, which eliminates acrylonitrile to generate the coupled dimer P(V) product. The vulnerable phosphite triester intermediate is bypassed entirely, making the methodology very suitable to solution-phase synthesis. This new coupling protocol requires no protection of the 5'-OH function and provides a new method of installing internucleosidic phosphorodiamidate bonds with near quantitative yields.
Databáze: OpenAIRE