Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study

Org Lett. 2005 Dec 8;7(25):5645-8. doi: 10.1021/ol052270y.

Abstract

[chemical reaction: see text]. We report here the synthesis of the 5'-[benzhydryloxybis(trimethylsilyloxy)]silyl-2'-methylseleno-2'-deoxyuridine phosphoramidite and its incorporation into oligonucleotides by solid-phase synthesis. The coupling yield of this phosphoramidite into oligonucleotides is higher than 99%. We also demonstrate that this 2'-methylselenophosphoramidite is compatible with the 5'-silyl-2'-ACE chemistry, for longer Se-RNA solid-phase synthesis. Our preliminary NMR study on the synthesized 2'-Se-DNA has revealed a U(Se)-A base pair and a duplex structure formation when its complementary strand was present.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemical synthesis
  • Deoxyuridine / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemical synthesis*
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis

Substances

  • 5'-(benzhydryloxybis(trimethylsilyloxy))silyl-2'-methylseleno-2'-deoxyuridine phosphoramidite
  • Oligonucleotides
  • Organophosphorus Compounds
  • Organoselenium Compounds
  • uridine phosphoramidite
  • Deoxyuridine
  • Uridine