Synthesis of threose nucleic acid (TNA) phosphoramidite monomers and oligonucleotide polymers.

Center for Evolutionary Medicine and Informatics, The Biodesign Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona, USA.

Current protocols in nucleic acid chemistry / edited by Serge L. Beaucage ... [et al.] 2012 Sep

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This unit describes the preparation of dimethoxytrityl (DMTr)-protected α-L-threofuranosyl 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. Vorbrüggen-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.

Citation

Su Zhang, John C Chaput. Synthesis of threose nucleic acid (TNA) phosphoramidite monomers and oligonucleotide polymers. Current protocols in nucleic acid chemistry / edited by Serge L. Beaucage ... [et al.]. 2012 Sep;Chapter 4:Unit4.51