6339-80-6Relevant academic research and scientific papers
Synthesis of 2-Thioorotidine and Comparison of Its Unusual Instability with Its Canonical Pyrimidine Counterparts
Kumar, Ravi,Springsteen, Greg,Krishnamurthy, Ramanarayanan
, p. 14427 - 14435 (2019)
2-Thiopyrimidine nucleosides exhibit properties that are interesting from both a biological/medicinal and origins of life chemistry point of view. We report here the first synthesis of the nucleoside 2-thioorotidine and our observations on its unexpected lability with respect to its N-glycosidic bond when compared with its corresponding canonical pyrimidine counterparts. We hypothesize that the cause of the lability of the N-glycosidic bond is due to the combined steric and electronic effects from the 2-thio- and the 6-carboxyl groups, a lability that could, in turn, be useful for further chemical transformations.
