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UV IRRADIATION OF NUCLEIC ACIDS: CHARACTERIZATION OF PHOTOPRODUCTS OF THYMIDYLYL‐(3′→5′)‐2′‐DEOXY‐5‐FLUOROURIDINE
Author(s) -
Alderfer James L.,
Soni SunilD.,
Arakali Aruna V.,
Wallace John C.
Publication year - 1993
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1993.tb09209.x
Subject(s) - nucleic acid , chemistry , irradiation , characterization (materials science) , radiochemistry , combinatorial chemistry , biochemistry , nanotechnology , materials science , physics , nuclear physics
— The acetone‐sensitized irradiation using UV‐B (ultraviolet light, 280–320 nm; sunlamps) of thymidyl‐yl(3′→5′)deoxyfluorouridine monophosphate produces two main photoproducts. The distribution of these photo‐products 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.