title: Chemical phosphorylation of deoxyribonucleosides and thermolytic DNA oligonucleotides.
abstract: The phosphorylating reagent bis[S-(4,4'-dimethoxytrityl)-2-mercaptoethyl]-N,N-diisopropylphosphoramidite is prepared in three steps from commercial methyl thioglycolate and diisopropylphosphoramidous dichloride. The phosphorylating reagent has been used successfully in the solid-phase synthesis of deoxyribonucleoside 5'-/3'-phosphate or -thiophosphate monoesters and oligonucleotide 5'-phosphate/-thiophosphate monoesters. Bis[S-(4,4'-dimethoxytrityl)-2-mercaptoethyl]-N,N-diisopropylphosphoramidite has also been employed in the construction of a thermolytic dinucleotide prodrug model to evaluate the ability of the reagent to produce thermosentive oligonucleotide prodrugs under mild temperature conditions ( approximately 25 degrees C) for potential therapeutic applications.
authors.affiliation: Center for Drug Evaluation and Research, Food and Drug Administration, Bethesda, Maryland, USA.
authors.forename: Cristina
authors.initials: C
authors.lastname: Ausín
authors.forename: Andrzej
authors.initials: A
authors.lastname: Grajkowski
authors.forename: Jacek
authors.initials: J
authors.lastname: Cieślak
authors.forename: Serge L
authors.initials: SL
authors.lastname: Beaucage
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000737:chemistry*; D010766:Phosphorylation
chemical_list: D003853:Deoxyribonucleosides; D004247:DNA