Skip to main content

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

  • Chapter
Biological Reactive Intermediates IV

Part of the book series: Advances in Experimental Medicine and Biology ((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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Pagano, D.A., Yagen, B., Hernandez, O., Bend, J.R., Zeiger, E. (1982). Mutagenicity of (R) and (S) styrene 7,8-oxide and the intermediary mercapturic acid metabolites formed from styrene 7,8-oxide. Environ. Mutagenesis 4, 575–584.

    Article  CAS  Google Scholar 

  • Peter, H., Csankly, G. (1990). A note on the preference of aliphatic epoxides for the N-7 position of guanine in DNA. Arch. Toxicol.,in press

    Google Scholar 

  • Uhlenbeck, O.C., Baller, J., Doty, P. (1970). Complementary oligonucleotide binding to the anticodon loop of fMet-transfer RNA. Nature 225, 508–510.

    Article  CAS  PubMed  Google Scholar 

  • Wistuba, D., Nowotny, H.P., Trager, O., Schurig, V. (1989). Cytochrome P-450- catalyzed asymmetric epoxidation of simple prochiral and chiral aliphatic alkenes: species dependence and effect of enzyme induction on enantioselective oxirane formation. Chirality 1, 127–136.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Peter, H., Marczynski, B., Wistuba, D., Szentpály, L.V., Csanády, G., Bolt, H.M. (1991). Chiral Epoxides, their Enantioselective Reactivity Towards Nucleic Acids, and a First Outline of a Quantum Chemical Structure-Reactivity Calculation. In: Witmer, C.M., Snyder, R.R., Jollow, D.J., Kalf, G.F., Kocsis, J.J., Sipes, I.G. (eds) Biological Reactive Intermediates IV. Advances in Experimental Medicine and Biology, vol 283. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5877-0_108

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5877-0_108

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5879-4

  • Online ISBN: 978-1-4684-5877-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics