Oligonucleotides containing a 3'-S-phosphorothiolate linkage provide valuable analogues for exploring the mechanisms of ribozyme-catalyzed reactions. Since 3'-S-modified RNAs are very liable to hydrolysis, the synthesis and storage remain challenging. The introduction of 2'-O-photoliable group could be helpful to increase the stability of these 3'-S-modified RNAs during storage and handling.  To construct oligonucleotides containing a 2'-O-(o-nitrobenzyl)-3'-S-guanosine nucleotide via solid-phase synthesis, an efficient approach for the synthesis of 2'-O-(o-nitrobenzyl)-3'-thioguanosine phosphoramidite starting from guanosine in nine steps with 10.2% overall yield is developed.

Synthesis of the phosphoramidite derivative of 2'-O-(o-nitrobenzyl)-3'-thioguanosine

243rd National Meeting (2012)

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