Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: a backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography

Abstract

Stable selenium-modified DNA which maintains the native tertiary structure has been prepared under automated conditions enabling SAD X-ray crystallography.

Modified internucleoside linkages for nuclease-resistant oligonucleotides

“…Recently Conlon et al described the first solid-phase synthesis of phosphoroselenoate-ODN. 151 They exploited the work of Vyle to synthetize dinucleoside phosphoroselenoate triesters and upon subsequent phosphitylation introduced them into ODN. First, 5 0 -tosylthymidine 12 was converted into the corresponding 5 0 -selenocyanate 13 within 90 min under microwave irradiation.…”

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

“…Among the modified biomolecules, selenium-containing nucleotides demonstrate great advantages, mainly as a tool for studies of interactions with metal ions, protein-protein and protein-ligand, and other biomolecules, as RNA and DNA. [102,103,104,105,106] The selenium-modified nucleic acids (Figure 8), [107] and selenomethionine were prepared to study the protein folding. [108] In 2020, Nawrot and co-workers described the synthesis of 5-methylaminomethyl-2-selenouridines and the study of their properties toward base pairing with guanosine.…”

Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives

“…The presence of 2,6-lutidine served to improve the solubility of 100 in CH 3 CN, and all the dimers were obtained as diasteroisomers. Finally, the phosphitylation of the dimers allowed the preparation of the corresponding phosphoramidites 103 , which were then used as starting materials for the successive solid-state synthesis of oligomers, the actual target of these studies [ 93 , 94 ]. These selenium containing oligomers were used to observe conformational changes within nucleic acids during folding, recognition, and processing by applying the selenium single wavelength anomalous diffraction.…”