N3‘→P5‘ Oligodeoxyribonucleotide Phosphoramidates: A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction
The Journal of Organic Chemistry1997Vol. 62(21), pp. 7278–7287
Citations Over TimeTop 14% of 1997 papers
Jeffrey S. Nelson, Karen L. Fearon, Mark Q. Nguyen, Sarah N. McCurdy, Jeff E. Frediani, Michael F. Foy, Bernard L. Hirschbein
Abstract
A new method for the synthesis of N3'-->P5' phosphoramidate oligodeoxynucleotides is demonstrated. Described herein is the synthesis of the monomers utilized in the phosphoramidite amine-exchange process and the experimental details pertaining to this new mode of chain assembly. The phosphoramidite amine-exchange method generates coupling yields in the 92-95% range per cycle and further enables the synthesis of chimeric phosphoramidate/phosphodiester or phosphoramidate/phosphorothioate oligonucleotides with no instrument modifications.
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