With the explosion of new research in the field of RNA, a significant demand for synthesis of oligoribonucleotides has materialized thus allowing the phosphoramidite method to become a very valuable tool in biochemical research. As a result, the demand for synthesis of phosphoramidite monomers has increased. However, there is a lack of selectivity between the 2'- and 3'-hydroxyl groups in RNA for phosphite addition, resulting in a reduction in efficiency of synthesis.  Silyl protecting groups have been developed to improve selectivity for the 2'-hydroxyl; but, in order to obtain the greatest utility, yields of the monomer still need to be improved.  In order to improve these yields, we have developed structural analogs of the 5'-hydroxyl protecting group dimethoxytrityl (DMT) which contain linker arms aimed at improving selectivity for 3'-hydroxyl phosphitylation.  Synthetic methods for assembly of the protecting groups as well as computational models will be presented.

Novel RNA phosphoramidite monomer protecting groups: Synthesis and modeling analysis

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.