Postsynthetic Conjugation of RNA to Carboxylate and Dicarboxylate Molecules

Yossi Shemesh, Eylon Yavin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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.

Original languageAmerican English
Pages (from-to)753-762
Number of pages10
JournalNucleosides, Nucleotides and Nucleic Acids
Volume34
Issue number11
DOIs
StatePublished - 2 Nov 2015

Bibliographical note

Publisher Copyright:
Copyright © 2015 Taylor and Francis Group, LLC.

Keywords

  • Phosphate mimics
  • TMSE
  • carboxylate
  • dicarboxylate
  • solid phase RNA synthesis

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