Conformational studies of stereoisomeric tetraols serived form syn- and anti-dibenzo [a,l]pyrene diolepoxides

R. Jankowiak, F. Ariese, D. Zamzow, A. Luch, H. Kroth, A. Seidel, G.J. Small

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An understanding of the conformational behavior of the stereoisomeric tetrols at the 11,12,13,14-positions of dibenzo[a,l]pyrene (DB[a,l]P) is essential for the spectroscopic identification of DNA adducts derived from the biologically highly active fjord region syn- and anti-DB[a,l]P-11,12- diol 13,14-epoxides. Conformational effects are expected to play an important role in DNA-DB[a,l]P diol epoxide reactivity, base-sequence specificity, and conformation dependent repair. The results of conformational studies on trans-anti-, cis-anti-, and cis-syn-DB[a,l]P tetrol isomers are presented and compared to the results obtained previously for trans-syn-DB[a,l]P tetrol (Carcinogenesis 17, 829-837, 1996). Molecular mechanics, dynamical simulations, and semiempirical calculations of electronic transitions are used to interpret the low-temperature fluorescence spectra and
Original languageEnglish
Pages (from-to)677-686
JournalChemical Research in Toxicology
Publication statusPublished - 1997


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