title: Postsynthetic conjugation of RNA to carboxylate and dicarboxylate molecules.
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.
authors.affiliation: a School of Pharmacy, The Hebrew University of Jerusalem , Hadassah Ein-Kerem , Jerusalem , Israel.
authors.forename: Yossi
authors.initials: Y
authors.lastname: Shemesh
authors.affiliation: a School of Pharmacy, The Hebrew University of Jerusalem , Hadassah Ein-Kerem , Jerusalem , Israel.
authors.forename: Eylon
authors.initials: E
authors.lastname: Yavin
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D012313:RNA / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D012313:RNA
keywords: Phosphate mimics; TMSE; carboxylate; dicarboxylate; solid phase RNA synthesis