An organometallic route to oligonucleotides containing phosphoroselenoate

Geoffrey A. Holloway, Caroline Pavot, Stephen A. Scaringe, Yi Lu, Thomas B. Rauchfuss

Research output: Contribution to journalArticlepeer-review

Abstract

Unlike the widespread use of phosphorothioates in nucleic acid chemistry, complementary research on phosphoroselenoates has been severely limited. Previous routes to DNA and RNA that contain phosphoroselenoates employ elemental Se and KSeCN as Se transfer agents, although these reagents suffer from low or unselective reactivity. The metastability of the P-Se bond demands soluble, selective Se transfer reagents. The organometallic reagent (iPrC5H4)2TiSe5 satisfies these criteria, as we demonstrate by the synthesis of phosphoroselenoate derivatives of mono- and oligonucleotides of DNA and a dinucleotide of RNA. The new general method is compatible with high-throughput phosphoramidate oligonucleotide synthesis, which allows for the preparation of site-specifically labeled oligonucleotides. A 31P NMR spectroscopy study shows that the phosphoroselenoate of (5′)-d(GGAATGTCSeTGTCG)-(3′) selectively binds to soft Cd2+ ions but not Mg2+ ions.

Original languageEnglish (US)
Pages (from-to)1061-1065
Number of pages5
JournalChemBioChem
Volume3
Issue number11
DOIs
StatePublished - Nov 4 2002

Keywords

  • DNA
  • RNA
  • Selenium
  • Synthetic methods

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)

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