606972-26-3Relevant academic research and scientific papers
Sugar conformational effects on the photochemistry of thymidylyl(3′-5′)thymidine
Ostrowski, Tomasz,Maurizot, Jean-Claude,Adeline, Marie-Therese,Fourrey, Jean-Louis,Clivio, Pascale
, p. 6502 - 6510 (2003)
The synthesis and conformational analysis of 2′-O,5-dimethyluridylyl(3′-5′)-2′-O,5-dimethyluridine (1a), the analogue of thymidylyl(3′-5′)thymidine (TpT; 1b) in which a methoxy group replaces each 2′-α-hydrogen atom, are described. In comparison with TpT, such modification increases the population of the C3′-endo conformer of the sugar ring puckering at the 5′- and 3′-ends from 30 to 75% and from 37 to 66%, respectively. Photolyses of 1a and TpT at 254 nm are qualitatively comparable (the cis-syn cyclobutane pyrimidine dimer and the (6-4) photoproduct are formed), although it is significantly faster in the case of 1a. These results are explained by the increased propensity of the modified dinucleotide to adopt a base-stacked conformation geometry reminiscent of that for TpT.
