Carcinogen–base stacking and base–base stacking in dCpdG modified by (+) and (−) anti‐BPDE

Brian E. Hingerty, Suse Broyde

Research output: Contribution to journalArticlepeer-review


The low‐energy conformations accessible to dCpdG modified at guanine N2 via trans epoxide opening by (+) and (−) 7β,8α‐dihydroxy‐9α,10α‐epoxy‐7,8,9,10‐tetrahydrobenzo(a)pyrene (anti‐BPDE) have been delineated by minimized semiempirical potential‐energy calculations with all torsion angles flexible. Nearly 4000 trials were made, representing a fairly thorough investigation of the conformation space of the adducts. Carcinogen–base stacked states and base–base stacked conformers were found in the low‐energy regions of both enantiomers. Many ω′, ω, ψ domains accommodate the two types of conformations, with B‐like backbones among the most preferred states in each case. The conformational differences between the two enantiomers on the dimer level reside in subtle distinctions in orientation of the carcinogen–base linkage.

Original languageEnglish (US)
Pages (from-to)2279-2299
Number of pages21
Issue number12
StatePublished - Dec 1985

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Biomaterials
  • Organic Chemistry


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