γ-Radiolysis DNA Products: Synthesis of 6-(α-Thyminyl)-5,6-dihydro-4-thiothymine Derivatives
Abstract
Far-UV photolysis of 4-thiothymidylyl(3'-5')thymidine led to the formation of three stable derivatives: one resulting from a combination between a 3'-end methylene radical and a 5'-end C(4) radical [4-(alpha-thyminyl) derivative] and two formed after a combination between a 3'-end methylene radical and a 5'-end C(6) radical [6-(alpha-thyminyl) derivative]. In the latter series, two stereochemical pathways took place during the reaction between the methylene and C(6) radicals. The major pathway occurred when the 5'-base glycosidic bond had an anti conformation leading to an S configuration of the C(6) Tp-end. The minor pathway, which had never been reported before in this series, involved a 5'-base in a syn conformation leading consequently to the R configuration at the C(6) Tp-end. The 5,6-dihydrothymine moiety of these two adducts presented a 5,6-trans diaxial substitution that resulted from the epimerization, at the 5,6-dihydropyrimidine 5-position, of a less stable cis-disubstituted intermediate.
Related Papers
- → Synthetic Approaches for the Construction of Five- and Six-Membered Silaazacycles(2022)15 cited
- → Guadinomines, Type III Secretion System Inhibitors, Produced by Streptomyces sp. K01-0509(2008)44 cited
- → Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety(2016)26 cited
- Design, synthesis and evaluation of novel hydroxyethylamine derivatives with nitrogen heterocyclic moiety at N-terminal as BACE1 inhibitors(2010)
- STUDY ON INTRAMOLECULAR SYNERGISTIC INHIBITIVE EFFECTS OF BENZOTRIAZOLY MOIETY AND INIDAZOLY MOIETY(2009)