Isolation and characterization of pyrimidine-psoralen photoadducts from DNA

Journal Article · Fri May 01 04:00:00 EDT 1981 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja00399a035· OSTI ID:1077827

Straub, Kenneth ^[1]; Kanne, David ^[1]; Hearst, John E. ^[1]; Rapoport, Henry ^[1]

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1. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Univ. of California, Berkeley, CA (United States)

In this study, we have examined the photoadducts of 4'-hydroxymethyl-4,5',8-trirnethylpsoralen (HMT) and native DNA. Five nucleoside-HMT monoaddition products have been isolated and characterized, corresponding to three deoxythymidine-HMT and two deoxyuridine (derived from deoxycytidine)-HMT adducts. Structural assignments are based on high resolution mass spectrometry and ¹H NMR studies, including homonuclear spin decoupling and nuclear Overhauser effect (NOE) experiments. Our results indicate that (1) a limited number of nucleoside-psoralen adducts are formed with native, double-stranded DNA, and (2) the stereochemistry of the adducts is apparently determined by the geometry of the non-covalent intercalative complex formed by HMT and DNA prior to irradiation.

• Research Organization: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC02-05CH11231
• OSTI ID: 1077827
• Report Number(s): LBL--11582
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 9 Vol. 103; ISSN 0002-7863
• Publisher: American Chemical Society (ACS)
• Country of Publication: United States
• Language: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES