Synthesis of oligoribonucleotides containing 4-thiouridine using the convertible nucleoside approach and the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl group

Nucleosides Nucleotides Nucleic Acids. 2004;23(11):1767-77. doi: 10.1081/NCN-200034044.

Abstract

Oligoribonucleotides containing 4-thiouridine were prepared using the Fpmp group for protection of the 2'-OH. Two uridine derivatives with the 1,2,4-triazolyl and the 2-nitrophenyl groups at position 4 were used to obtain 4-thiouridine by postsynthetic substitution with sodium hydrogen sulfide. Both uridine derivatives allow the preparation of the desired oligonucleotides in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nucleosides / chemistry*
  • Oligoribonucleotides / chemical synthesis*
  • Oligoribonucleotides / chemistry
  • Oligoribonucleotides / metabolism
  • Piperidines / chemistry*
  • Thiouridine / chemistry*
  • Thiouridine / metabolism

Substances

  • 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl
  • Nucleosides
  • Oligoribonucleotides
  • Piperidines
  • Thiouridine