Abstract
Electron transfer involving nucleic acids and their derivatives is an important field in bioorganic chemistry, specifically in connection with its role in the photo-driven DNA damage and repair. Four-membered ring heterocyclic oxetanes and azetidines have been claimed to be the intermediates involved in the repair of DNA (6-4) photoproduct by photolyase. In this context, we examine here the redox properties of the two azetidine isomers obtained from photocycloaddition between 6-aza-1,3-dimethyluracil and cyclohexene. Steady-state and time-resolved fluorescence experiments using a series of photoreductants and photooxidants have been run to evaluate the efficiency of the electron transfer process. Analysis of the obtained quenching kinetics shows that the azetidine compounds can act as electron donors. Additionally, it appears that the cis isomer is more easily oxidized than its trans counterpart. This result is in agreement with electrochemical studies performed on both azetidine derivatives.
Highlights
Electron transfer involving nucleic acids and their derivatives has been the subject of extensive studies in bioorganic chemistry, primarily because of its role in DNA damage and repair, and in connection with the possible behavior of DNA as a molecular wire [1,2,3,4,5,6,7,8,9]
The initial electron transfer step assumed to be involved in the repair of thymine-cytosine
An efficient fluorescence quenching is observed for the cyanoaromatics DCN, DCA and CNN, both in steady-state and time-resolved experiments
Summary
Electron transfer involving nucleic acids and their derivatives has been the subject of extensive studies in bioorganic chemistry, primarily because of its role in DNA damage and repair, and in connection with the possible behavior of DNA as a molecular wire [1,2,3,4,5,6,7,8,9]. With triphenylazetidines, which are structurally unrelated to pyrimidine bases [21] This process for wasinvestigating studied by the steady-state fluorescence using a serieselectron of photosensitizers (PS, 1). The twostep azetidine isomers and 2b were synthesized and used as Both substrates for investigating the initial step in reductive oxidative electron transfer(PS, 1).). Electron donor and acceptor sensitizers were selected covering a large range of singlet excited state redox process was studied by steady-state fluorescence using a series of photosensitizers (PS, Figure 1).
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