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

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

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 2 , 2004

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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.

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

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Article Details

VOLUME: 1
ISSUE: 2
Year: 2004
Page: [183 - 188]
Pages: 6
DOI: 10.2174/1570178043488536
Price: $58

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