Nucleosides, Nucleotides & Nucleic Acids 2015-01-01

Postsynthetic conjugation of RNA to carboxylate and dicarboxylate molecules.

Yossi Shemesh, Eylon Yavin

Index: Nucleosides Nucleotides Nucleic Acids 34 , 753-62, (2015)

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Abstract

Carboxylates and dicarboxylates are important phosphate mimics. Herein, we present a simple synthetic route for the preparation of RNA carboxylate/dicarboxylate conjugates, starting from suitably protected NH2- and COOH-containing molecules that are coupled to the RNA on the solid support. The key point in our method was the use of trimethylsilylethanol (TMSE-OH) protecting group, which is removed simultaneously with the silyl protecting group on the 2'-OH of the RNA ribose (e.g. t-Butyldimethylsilyl) during the final RNA cleavage/deprotection steps. The usefulness of this method was demonstrated by preparing different RNA-phosphate mimics oligos.