Towards Oligonucleotide Pro-Drugs: 2,2-Bis(ethoxycarbonyl) and 2- (Alkylaminocarbonyl)-2-cyano Substituted 3-(Pivaloyloxy)Propyl Groups as Biodegradable Protecting Groups for Internucleosidic Phosphoromonothioate Linkages

Title: Towards Oligonucleotide Pro-Drugs: 2,2-Bis(ethoxycarbonyl) and 2- (Alkylaminocarbonyl)-2-cyano Substituted 3-(Pivaloyloxy)Propyl Groups as Biodegradable Protecting Groups for Internucleosidic Phosphoromonothioate Linkages

Volume: 1 Issue: 2

Author(s): P. Poijarvi, M. Oivanen and H. Lonnberg

Affiliation:

Keywords: oligonucleotides, antisense, biodegradable, protecting group, hydrolysis, phosphotriester

Abstract: The applicability of 2,2-bis(ethoxycarbonyl)-3-(pivaloyloxy)propyl and 2- cyano-2-(2-phenylethylaminocarbonyl)-3-(pivaloyloxy)propyl groups as biodegradable protecting agents for the internucleosidic linkages of phosphorothioate antisense oligonucleotides has been studied. For this purpose, protected phosphoromonothioates of thymidylyl-(3→5)-thymidine [Tp(s)T] containing either a bridged or non-bridged sulfur atom have been prepared, and their chemical stability and enzymatic deprotection have been studied.

Cite this article as:

Poijarvi P., Oivanen M. and Lonnberg H., Towards Oligonucleotide Pro-Drugs: 2,2-Bis(ethoxycarbonyl) and 2- (Alkylaminocarbonyl)-2-cyano Substituted 3-(Pivaloyloxy)Propyl Groups as Biodegradable Protecting Groups for Internucleosidic Phosphoromonothioate Linkages, Letters in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570178043488536