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Dr. Jacek Cieślak, Dr. Cristina Ausín, Dr. Andrzej Grajkowski and Dr. Serge L. Beaucage The 2-Cyano-2,2-dimethylethanimine-N-oxymethyl Group for the 2′-Hydroxyl Protection of Ribonucleosides in the Solid-Phase Synthesis of RNA Sequences Chemistry - A European Journal 19

Version of Record online: 18 FEB 2013 | DOI: 10.1002/chem.201204235

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Novel 2-RNA protection: The reaction of 2-cyano-2-methyl propanal with 2′-O-aminooxymethylribonucleosides leads to 2′-O-(2-cyano-2,2-dimethylethanimine-N-oxymethyl)ribonucleosides, which were then converted into their fully protected phosphoramidite derivatives (see scheme; DMTr=4,4′-dimethoxytrityl). These amidites were successfully employed in the solid-phase synthesis of three chimeric RNA sequences, each with a different purine/pyrimidine ratio. This approach is straightforward, efficient, and cost effective.

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