title: Synthesis of threose nucleic acid (TNA) phosphoramidite monomers and oligonucleotide polymers.
abstract: 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.
authors.affiliation: Center for Evolutionary Medicine and Informatics, The Biodesign Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona, USA.
authors.forename: Su
authors.initials: S
authors.lastname: Zhang
authors.forename: John C
authors.initials: JC
authors.lastname: Chaput
mesh_terms: D005663:Furans / Q000737:chemistry; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*
chemical_list: D005663:Furans; D009696:Nucleic Acids; D009705:Nucleosides; D009943:Organophosphorus Compounds; C434331:phosphoramidite