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A new method for introducing amidate linkages in oligonucleotides using phosphoramidite chemistry
1Isis Pharmaceuticals, Inc., Carlsbad, CA 92008, USA.
Bioorganic & Medicinal Chemistry Letters
|October 6, 1999
Abstract:
Cyanoethyl-protected phosphotriester links in oligonucleotides made with standard pophosporamidite chemistry were converted to pbosphoramidate linkages during oligonucleotide synthesis on solid support. The cyanoethyl group was removed with piperidine, and the resulting phosphodiester was activated with p-tosyl chloride. An amine nucleophile displaced the tosyl to yield a phosphoramidate linkage.