Photogeneration of 2-deoxyribonolactone in benzophenone-purine dyads. Formation of ketyl-C1' biradicals.
Photolysis of the title dyads under aerobic conditions leads to a 2-deoxyribonolactone derivative. Laser flash photolysis reveals that the process occurs from the short-lived benzophenone-like triplet excited state. A mechanism involving intramolecular electron transfer with the purine bases (adenine, guanine, or 8-oxoadenine) as donors is proposed.
Paris
Cecilia
C
Instituto de Tecnología Química UPV-CSIC/Departamento de Química, Universidad Politécnica de Valencia, Avenida de los Naranjos S/N, 46022 Valencia, Spain.
Encinas
Susana
S
Belmadoui
Nourreddine
N
Climent
María J
MJ
Miranda
Miguel Angel
MA
D001577:Benzophenones / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D011687:Purines / Q000737:chemistry*; D013053:Spectrophotometry; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
D001577:Benzophenones; D005609:Free Radicals; D007659:Ketones; D011687:Purines; D013400:Sugar Acids; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone; C047723:benzophenone; C030985:purine