Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine

Bioorg Med Chem Lett. 2000 Aug 21;10(16):1795-8. doi: 10.1016/s0960-894x(00)00342-5.


A new method for the synthesis of 2'-O-methyl-2-thiouridine (s2Um) found in thermophilic bacterial tRNA was developed. Structural properties of s2Um and s2Um(p)U were studied by using 1H NMR spectroscopy. A modified nonaribonucleotide (RNA*: 5'-CGUUs2UmUUGC-3') was synthesized to study the base-recognition ability of s2Um in formation of RNA-RNA and RNA DNA duplexes. The UV melting experiments revealed that RNA*-RNA and RNA*-DNA duplexes having an s2U-A base pair are more stable than those having a U-A base pair. On the contrary, the thermal stability of RNA*-RNA and RNA*-DNA duplexes having an s2U-G wobble base pair was much lower than that of the unmodified duplexes having a natural U-G base pair. It is concluded that s2Um has higher selectivity toward A over G than unmodified U.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Archaea / genetics
  • Base Pairing
  • DNA / chemistry
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleic Acid Conformation
  • Nucleic Acid Heteroduplexes
  • Nucleic Acid Hybridization*
  • Oligoribonucleotides / chemistry*
  • Oligoribonucleotides, Antisense
  • RNA / chemistry
  • Thermodynamics
  • Thiouridine / analogs & derivatives*
  • Thiouridine / chemical synthesis*
  • Thiouridine / chemistry


  • 2'-O-methyl-2-thiouridine
  • Nucleic Acid Heteroduplexes
  • Oligoribonucleotides
  • Oligoribonucleotides, Antisense
  • Thiouridine
  • RNA
  • DNA