A novel protecting strategy for internucleosidic phosphate and phosphorothioate groups.
The utility of 2-(N-isopropyl-N-anisoylamino)ethyl group for protection of internucleosidic phosphate linkages in oligonucleotide synthesis was studied. The group demonstrated high coupling yields, favorable deprotection kinetics and a high hydrolytic stability of phosphoramidite building blocks. The mechanism of deprotection was established using a model phosphate triester.
Guzaev
A P
AP
Department of Medicinal Chemistry, Isis Pharmaceuticals, 2292 Faraday Ave., Carlsbad, California 92008, USA.
Manoharan
M
M
D009841:Oligonucleotides / Q000138:chemical synthesis*; D010755:Organophosphates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis; D013873:Thionucleotides / Q000138:chemical synthesis*
D009841:Oligonucleotides; D010755:Organophosphates; D009943:Organophosphorus Compounds; D013873:Thionucleotides; C434331:phosphoramidite