UNIT 13.6 Chemical Phosphorylation of Deoxyribonucleosides and Thermolytic DNA Oligonucleotides
Published Online: 1 OCT 2006
Copyright © 2006 by John Wiley & Sons, Inc.
Lab Protocol Title
Current Protocols in Nucleic Acid Chemistry
How to Cite
Ausín, C., Grajkowski, A., Cieślak, J. and Beaucage, S. L. 2006. Chemical Phosphorylation of Deoxyribonucleosides and Thermolytic DNA Oligonucleotides. Current Protocols in Nucleic Acid Chemistry. 26:13.6:13.6.1–13.6.21.
- Published Online: 1 OCT 2006
- Published Print: SEP 2006
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 (∼25°C) for potential therapeutic applications.
- thermolytic oligonucleotide prodrugs;
- solid-phase oligonucleotide synthesis