154084-96-5Relevant articles and documents
A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides
Chino, Marco,D'Alonzo, Daniele,De Fenza, Maria,Esposito, Anna,Guaragna, Annalisa,Palumbo, Giovanni,Talarico, Giovanni,di Giovanni, Concetta
, (2020/02/20)
A highly regio- and stereoselective route to d- and l-cyclohexenyl nucleosides has been devised, using the Tsuji–Trost reaction as the key step. Contrarily to the widely accepted mechanism (involving a net retention of configuration), the reaction proceeded in a highly stereoconvergent manner, providing cis nucleosides regardless of the relative configuration of the starting materials. DFT calculations confirmed the experimental data while suggesting the origin of the stereochemical reaction outcome.
Oligonucleotides containing a ribo-configured cyclohexanyl nucleoside: probing the role of sugar conformation in base pairing selectivity
Paolella, Concetta,D'Alonzo, Daniele,Schepers, Guy,Van Aerschot, Arthur,Di Fabio, Giovanni,Palumbo, Giovanni,Herdewijn, Piet,Guaragna, Annalisa
, p. 10041 - 10049 (2015/10/12)
The synthesis and a preliminary evaluation of the pairing properties of ribo-cyclohexanyl nucleic acids (r-CNA) is herein reported. Incorporation of a single r-CNA nucleotide into natural duplexes did not enhance their stability, while a very high pairing selectivity for RNA was found. As deduced by comparative analysis of Tm and NMR data, a relationship between pairing selectivity and conformational preferences of the "sugar" moiety of r-CNA (and more generally of six-membered nucleic acids) was suggested.
