Sugar conformational effects on the photochemistry of thymidylyl(3'-5')thymidine |
| |
Authors: | Ostrowski Tomasz Maurizot Jean-Claude Adeline Marie-Thérèse Fourrey Jean-Louis Clivio Pascale |
| |
Affiliation: | Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif sur Yvette, France. |
| |
Abstract: | 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'-alpha-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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|