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Molecules 2016, 21(12), 1683; doi:10.3390/molecules21121683

Stereoselective Fluorescence Quenching in the Electron Transfer Photooxidation of Nucleobase-Related Azetidines by Cyanoaromatics

Instituto Mixto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València—Consejo Superior de Investigaciones Científicas, Avda de los Naranjos s/n, 46022 Valencia, Spain
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Academic Editor: Carlos E. Crespo-Hernández
Received: 15 October 2016 / Revised: 29 November 2016 / Accepted: 1 December 2016 / Published: 7 December 2016
(This article belongs to the Special Issue Experimental and Computational Photochemistry of Bioorganic Molecules)
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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. View Full-Text
Keywords: DNA repair; energy and charge transfer; nucleobase analogues; photolyase; redox potential DNA repair; energy and charge transfer; nucleobase analogues; photolyase; redox potential
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Fraga-Timiraos, A.B.; Rodríguez-Muñiz, G.M.; Peiro-Penalba, V.; Miranda, M.A.; Lhiaubet-Vallet, V. Stereoselective Fluorescence Quenching in the Electron Transfer Photooxidation of Nucleobase-Related Azetidines by Cyanoaromatics. Molecules 2016, 21, 1683.

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