185141-91-7Relevant academic research and scientific papers
The synthesis of 2′-C-functionalised nucleosides for incorporation into catalytic RNA
Lawrence, Anthony J.,Pavey, John B.J.,O'Neil, Ian A.,Cosstick, Richard
, p. 1497 - 1501 (2007/10/03)
Five 2′-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed. Copyright
Synthesis and properties of 2'-deoxy-2'-α-C-branched nucleosides and nucleotides
Lawrence,Pavey,Cosstick,O'Neil
, p. 9213 - 9222 (2007/10/03)
Four functionalized 2'-deoxy-2'-α-C-branched nucleosides, namely, 2'-deoxy-2)-α-C-(carboxymethyl)uridine, 2'-deoxy-2'-α-C-acetamidouridine, 2'-deoxy-2'-α-C-(hydroxyethyl)uridine, and 2'-deoxy-2'α-C-(2,3-dihydroxypropyl)uridine, have been prepared. Conversion of these nucleosides to their appropriately protected phosphoramidites, followed by tetrazole-induced reaction with 2',3'-di-O-acetyluridine, oxidation, and subsequent deprotection furnished the corresponding dinucleoside monophosphates. During the oxidation of the amide-derived phosphite, partial dehydration occurred to give a mixture of the amide- and nitrile-containing dimers. Interestingly, the ratio of amide to nitrile could be largely controlled by choice of oxidant. The hydroxyethyl- and dihydroxypropyl-modified dimers were particularly resistant to snake venom phosphodiesterase-catalyzed hydrolysis (relative half-lives of 129 and 120, respectively, in comparison to UpU). It is anticipated that these nucleoside analogues will ultimately be used in the construction of ribozymes containing enhanced functionality and nuclease resistance.
