1629048-13-0Relevant articles and documents
A family of click nucleosides for metal-mediated base pairing: Unravelling the principles of highly stabilizing metal-mediated base pairs
Richters, Tim,Krug, Olga,Koesters, Jutta,Hepp, Alexander,Mueller, Jens
, p. 7811 - 7818 (2014)
A family of artificial nucleosides has been developed by applying the CuI-catalyzed Huisgen 1,3-dipolar cycloaddition. Starting from 2-deoxy-β-D-glycosyl azide as a common precursor, three bidentate nucleosides have been synthesized. The 1,2,3-triazole involved in all three nucleobases is complemented by 1,2,4-triazole (TriTri), pyrazole (TriPyr), or pyridine (TriPy). Molecular structures of two metal complexes indicate that metal-mediated base pairs of TriPyr may not be fully planar. An investigation of DNA oligonucleotide duplexes comprising the new click nucleosides showed that they can bind AgI to form metal-mediated base pairs. In particular the mispair formed from TriPy and the previously established imidazole nucleoside is significantly stabilized in the presence of Ag I. A comparison of different oligonucleotide sequences allowed the determination of general factors involved in the stabilization of nucleic acids duplexes with metal-mediated base pairs. Artificial base pairs: The application of three closely related triazole-derived artificial nucleosides in metal-mediated base pairing is described (see figure). Depending on the complementary nucleoside, [2+2] and [2+1] coordination modes are possible. The investigation of different oligonucleotide sequences has enabled the derivation of general principles underlying the formation of highly stabilizing metal-mediated base pairs.