Excited state enantiodifferentiating interactions between a chiral benzophenone derivative and nucleosides.
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.
Lhiaubet-Vallet
Virginie
V
Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Avda de Los Naranjos s/n, 46022 Valencia, Spain.
Encinas
Susana
S
Miranda
Miguel A
MA
D004247:DNA / Q000737:chemistry / Q000528:radiation effects; D003849:Deoxyguanosine / Q000737:chemistry / Q000528:radiation effects; D005609:Free Radicals / Q000737:chemistry; D007660:Ketoprofen / Q000737:chemistry* / Q000528:radiation effects*; D007700:Kinetics; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry* / Q000528:radiation effects*; D010782:Photolysis; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013997:Time Factors
D005609:Free Radicals; D009705:Nucleosides; D004247:DNA; D007660:Ketoprofen; D003849:Deoxyguanosine