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Nucleic Acids Symposium Series 2008 52(1):55-56; doi:10.1093/nass/nrn028
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© 2008 Oxford University Press

This article appears in the following Nucleic Acid Symposium Series issue: Joint Symposium of the 18th International Roundtable on Nucleosides, Nucleotides and Nucleic Acids and the 35th International Symposium on Nucleic Acids Chemistry [View the issue table of contents]

Recent Developments in the Synthesis of RNA Oligonucleotides for Potential Therapeutic Applications.

Jacek Cieslak, Andrzej Grajkowski, Cristina Ausín and Serge L. Beaucage*

Division of Therapeutic Proteins, Center for Drug Evaluation and Research, Food and Drug Administration, 8800 Rockville Pike, Bethesda, Maryland, USA

*Corresponding Author.E-mail: Serge.Beaucage{at}fda.hhs.gov

Abstract

The 4-(N-dichloroacetyl-N-methylamino)benzyloxymethyl group for 2'-hydroxyl protection has been successfully employed in the solid-phase synthesis of AUCCGUAGCUAACGUCAUGG. The use of the 2'-Omethylthiomethyl (2'-O-MTM) protecting group in the development of a cost effective approach to RNA synthesis has been evaluated through the solid-phase synthesis of [2'-O-MTM U]19dT. Given the sensitivity of 2'-thioacetals to acidic conditions, the base-labile [2-(9- fluorenyl)propyl-2-oxy]carbonyl group for 5'-Oprotection of ribonucleosides has been designed to accommodate the synthesis of oligoribonucleotides functionalized with 2'-thioacetal groups.


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