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



: Poijarvi P, Oivanen M, Lonnberg H

Publisher: BENTHAM SCIENCE PUBL LTD

: 2004

 Letters in Organic Chemistry

: LETTERS IN ORGANIC CHEMISTRY

: LETT ORG CHEM

: 1

: 2

: 183

: 188

: 6

: 1570-1786

DOI: https://doi.org/10.2174/1570178043488536


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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