title: UV irradiation of nucleic acids: characterization of photoproducts of thymidylyl-(3'-->5')-2'-deoxy-5-fluorouridine.
abstract: The acetone-sensitized irradiation using UV-B (ultraviolet light, 280-320 nm; sunlamps) of thymidylyl(3'-->5')deoxyfluorouridine monophosphate produces two main photoproducts. The distribution of these photoproducts is dependent on the pH of the irradiation solution. At pH 6, the cis-syn cyclobutane-type photodimer is the major product, whereas at high pH (8-10) a photoadduct is the major product. These photoproducts have been identified and structurally characterized by H-1 and C-13 NMR spectroscopy. The photoadduct arises from defluorination of the 5-fluorouracil moiety. The structure of the photoadduct maintains the sugar-phosphate backbone of the starting material (d-TpF), and contains a saturated thymine moiety with an added Thy(C6-hydroxyl) and a Thy(C5)-(C5)Ura covalent bond.
authors.affiliation: Biophysics Department, Roswell Park Cancer Institute, Buffalo, NY 14263.
authors.forename: J L
authors.initials: JL
authors.lastname: Alderfer
authors.forename: S D
authors.initials: SD
authors.lastname: Soni
authors.forename: A V
authors.initials: AV
authors.lastname: Arakali
authors.forename: J C
authors.initials: JC
authors.lastname: Wallace
mesh_terms: D002851:Chromatography, High Pressure Liquid; D015226:Dinucleoside Phosphates / Q000528:radiation effects*; D004307:Dose-Response Relationship, Radiation; D005467:Floxuridine / Q000031:analogs & derivatives* / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D011740:Pyrimidine Dimers; D014466:Ultraviolet Rays
chemical_list: D015226:Dinucleoside Phosphates; D011740:Pyrimidine Dimers; D005467:Floxuridine; C082163:thymidylyl-(3'-5')-2'-deoxy-5-fluorouridine; C017758:thymidylyl-(3'-5')-thymidine