Site-selected incorporation of 5-carboxymethylaminomethyl(-2-thio)uridine into RNA sequences by phosphoramidite chemistry

Org Biomol Chem. 2014 Feb 21;12(7):1052-6. doi: 10.1039/c3ob42302f.

Abstract

5-Carboxymethylaminomethyluridine (cmnm(5)U) and 5-carboxymethylaminomethyl-2-thiouridine (cmnm(5)s(2)U) are located at the wobble position in several cytosolic and mitochondrial tRNA sequences. In this paper, we report the first site-selected incorporation of cmnm(5)U and cmnm(5)s(2)U into RNA sequences by phosphoramidite chemistry on a CPG solid support. Trifluoroacetyl and 2-(trimethylsilyl)ethyl were selected for the protection of the amine and carboxyl functions, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • RNA / chemistry*
  • Thiouridine / analogs & derivatives*
  • Thiouridine / chemistry

Substances

  • Organophosphorus Compounds
  • phosphoramidite
  • Thiouridine
  • RNA
  • Glycine