@article{sochacka_2001, title={Efficient assessment of modified nucleoside stability under conditions of automated oligonucleotide synthesis: Characterization of the oxidation and oxidative desulfurization of 2-thiouridine}, volume={20}, ISSN={["1525-7770"]}, DOI={10.1081/NCN-100107198}, abstractNote={In order to efficiently assess the chemical stability of modified nucleosides to the reagents and conditions of automated oligonucleotide synthesis, we designed, developed and tested a scheme in which the modified nucleoside, directly attached to a solid support, is exposed to the cyclic chemistry of the instrument. Stability of 2-thiouridine against different oxidizers was investigated. Tertbutyl hydroperoxide (1 M) in anhydrous acetonitrile was a more effective oxidizer for the incorporation of 2-thiouridine into oligonucleotide chains than the same oxidizer in methylene chloride. Carbon tetrachloride/water in the presence of a basic catalyst was superior in maintaining the thiocarbonyl function, but its utility for RNA synthesis has yet to be fully tested, whereas 2-phenylsulfonyloxaziridine was a very efficient reagent for oxidative desulfurization of 2-thiouridine.}, number={10-11}, journal={NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS}, author={Sochacka, E}, year={2001}, pages={1871–1879} }