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Chiral Epoxides, their Enantioselective Reactivity Towards Nucleic Acids, and a First Outline of a Quantum Chemical Structure-Reactivity Calculation

  • H. Peter
  • B. Marczynski
  • D. Wistuba
  • L. V. Szentpály
  • G. Csanády
  • H. M. Bolt
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 283)

Abstract

Liver microsomes of mice, rats and humans metabolize prochiral vinyl precursors to chiral epoxides with different ratios for the two enantiomers (Wistuba et al. 1989), which may interact in different ways with chiral structures in the cell. Thus, the pharmacological effects of chiral pharmaceutics (L-Dopa, D-Penicillamine) are known to depend on the configuration of the molecule. A similar enantioselectivity may therefore modulate genotoxicity of metabolically formed chiral epoxides when they react with chiral (in terms of their conformation) macromolecular nucleic acids.

Keywords

Circular Dichroism Spectrum Propylene Oxide Equilibrium Dialysis Styrene Oxide Pure Enantiomer 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

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Copyright information

© Plenum Press, New York 1991

Authors and Affiliations

  • H. Peter
    • 1
  • B. Marczynski
    • 1
  • D. Wistuba
    • 1
    • 2
  • L. V. Szentpály
    • 1
    • 3
  • G. Csanády
    • 1
  • H. M. Bolt
    • 1
  1. 1.Inst. of Occup. Health at the University of DortmundDortmundGermany
  2. 2.Inst. Org. Chem.University of TübingenTübingenGermany
  3. 3.Chem. Dept.Univ. of the West IndiesJamaicaUSA

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