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

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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: antisense; biodegradable; hydrolysis; oligonucleotides; phosphotriester; protecting group

Document Type: Review Article


Affiliations: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.

Publication date: April 1, 2004

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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