Structure of a psoralen-thymine monoadduct formed in photoreaction with DNA |
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Authors: | Seth Peckler Bradford Graves David Kanne Henry Rapoport John E Hearst Sung-Hou Kim |
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Institution: | Department of Chemistry and Lawrence Berkeley Laboratories University of California Berkeley, Calif. 94720, U.S.A. |
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Abstract: | A photoreaction product between calf thymus DNA and 8-methoxypsoralen, a naturally occurring psoralen, was hydrolyzed with acid to isolate a major species of the reaction, 8-methoxypsoralen-thymine monoadduct. The crystal structure of the monoadduct has been determined. The structure confirms the results of other spectroscopic studies and allows one to conclude or suggest that: (1) the photoreaction occurs preferentially at both T-A and A-T sequences in natural DNA; (2) the photocrosslink introduces a substantial kink in the DNA structure; (3) the configuration of the photoproduct is “cis-syn” at both ends of the psoralen; (4) the thymine and psoralen moieties remain planar even after the photoreaction; and (5) the angle between psoralen and thymine in the photoproducts is not fixed but has a limited range of flexibility. |
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