Excited state enantiodifferentiating interactions between a chiral benzophenone derivative and nucleosides |
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Authors: | Lhiaubet-Vallet Virginie Encinas Susana Miranda Miguel A |
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Affiliation: | Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Avda de Los Naranjos s/n, 46022 Valencia, Spain. |
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Abstract: | Time-resolved measurements using nanosecond laser flash photolysis have revealed significant enantiodifferentiation in the interaction between ketoprofen (a chiral benzophenone derivative) and two relevant nucleosides, namely, thymidine and 2'-deoxyguanosine. In both cases, the highest quenching rate constants have been observed for (R)-ketoprofen, the enantiomer with lower pharmacological activity. Photoproduct studies performed in the case of thymidine suggest that the enantiodifferentiating process corresponds to a Paterno-Büchi reaction, leading to the formation of oxetanes. With 2'-deoxyguanosine, the quenching is associated with an electron-transfer process monitored through the generation of a ketyl radical. |
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