As greater attention has been placed on the role of RNAs in post-transcriptional processing, a desire for customized synthesis of oligoribonucleotides has garnered great interest. Solid phase synthesis has proven to be an effective and efficient technique for DNA synthesis, but a lack of regioselectivity between the 2’- and 3’-hydroxyl (OH) groups of RNA results in an undesired regioisomer, reducing yield.  Silyl protecting groups have been developed to increase selectivity for the 2’-OH group, but the synthetic route to phosphoramidite monomers must be streamlined. The goal of our research is to create structural analogs of the 5’-OH protecting group, dimethoxytrityl (DMT), with linker arms designed to increase the selectivity of the 3’-OH group for phosphitylation.  Synthetic methods for assembly of the 5’-OH protecting groups as well as computational models will be presented.

Novel synthetic tools for phosphoramidite regioselectivity in the synthesis of RNA monomers

251st National Meeting (2016)

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