Synthesis of a 3-methyluridine phosphoramidite to investigate the role of methylation in a ribosomal RNA hairpin

Bioorg Med Chem. 2002 Feb;10(2):325-32. doi: 10.1016/s0968-0896(01)00283-8.


The synthesis of a 5'-O-BzH-2'-O-ACE-protected-3-methyluridine phosphoramidite is reported [BzH, benzhydryloxy-bis(trimethylsilyloxy)silyl; ACE, bis(2-acetoxyethoxy)methyl]. The phosphoramidite was employed in solid-phase RNA synthesis to generate a series of RNA hairpins containing single or multiple modifications, including the common nucleoside pseudouridine. Three 19-nucleotide hairpin RNAs that represent the 1920-loop region (G(1906)-C(1924)) of Escherichia coli 23S ribosomal RNA were generated. Modifications were present at positions 1911, 1915, and 1917. The stabilities and structures of the three RNAs were examined by using thermal melting, circular dichroism, and NMR spectroscopy

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Nucleic Acid Conformation
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • RNA, Ribosomal / chemistry*
  • RNA, Ribosomal / metabolism*
  • RNA, Ribosomal, 23S / chemistry
  • RNA, Ribosomal, 23S / metabolism
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis*
  • Uridine / chemistry


  • 3-methyluridine phosphoramidite
  • Organophosphorus Compounds
  • RNA, Ribosomal
  • RNA, Ribosomal, 23S
  • 3-methyluridine
  • Uridine