A1 Refereed original research article in a scientific journal
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
Authors: Poijarvi P, Oivanen M, Lonnberg H
Publisher: BENTHAM SCIENCE PUBL LTD
Publication year: 2004
Journal:: Letters in Organic Chemistry
Journal name in source: LETTERS IN ORGANIC CHEMISTRY
Journal acronym: LETT ORG CHEM
Volume: 1
Issue: 2
First page : 183
Last page: 188
Number of pages: 6
ISSN: 1570-1786
DOI: https://doi.org/10.2174/1570178043488536
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.
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.
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