Synthesis of threose Nucleic Acid (TNA) phosphoramidite monomers and oligonucleotide polymers

Su Zhang, John C. Chaput

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


This unit describes the preparation of dimethoxytrityl (DMTr)-protected α-Lthreofuranosyl nucleic acid (TNA) phosphoramidite monomers for A, C, G, T, and diaminopurine, as well as their incorporation into TNA oligonucleotides by solid-phase synthesis. Starting from commercially available L-ascorbic acid, the protected threofuranosyl sugar is obtained in four steps. Vorbr̈uggen-Hilbert-Johnson glycosylation affords the desired threofuranosyl nucleosides, which are converted to their corresponding DMTr-protected phosphoramidite nucleosides in four additional steps. Phosphoramidite monomers are then used to construct TNA oligonucleotides by solid-phase synthesis using a standard DNA synthesizer. Curr. Protoc. Nucleic Acid Chem. 50:4.51.1-4.51.26.

Original languageEnglish (US)
Article number4.51
JournalCurrent Protocols in Nucleic Acid Chemistry
Issue numberSUPLL.50
StatePublished - Sep 2012


  • Alternative nucleic acids (ANA)
  • Chemical synthesis
  • Oligonucleotide
  • Solid-phase synthesis
  • Threose nucleic acid (TNA)
  • phosphoramidite

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry


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