Thio- and Seleno-Dioxaphosphorinane-Constrained Dinucleotides (D-CNA): Synthesis and Conformational Study

Article abstract of DOI:10.1002/ejoc.201601568

Thio- and seleno-α,β- and α,β,γ-D-CNA (constrained nucleic acid) dinucleotides in which two or three torsion angles of the sugar/phosphate backbone are controlled within a dioxaphosphorinane structure have been prepared. Their structural determination was carried out by means of NMR spectroscopy to show only slight variation on the torsion-angle control in comparison with their oxo analogues. Unexpected selenium migration has been pointed out from selenophosphotriester moiety to phosphoramidite group, but this drawback can be overcome using H-phosphonate chemistry.