Reaction kinetics of alkyl epoxides with DNA and other nucleophiles

Chem Biol Interact. 1994 Oct;93(1):51-8. doi: 10.1016/0009-2797(94)90085-x.

Abstract

1,2-Epoxy alkanes from C3 to C8 were reacted with DNA, deoxyguanosine and 4-(p-nitrobenzyl) pyridine (NBP). DNA was hydrolyzed at neutral pH to release 7-alkylguanines. The products were analyzed by HPLC. The epoxides reacted largely according to the chain length, shorter epoxides being more reactive. Substitutions through carbon 1 predominated. Reactivity with NBP was almost equal between the epoxides.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Chromogenic Compounds
  • DNA / chemistry*
  • Deoxyguanosine / chemistry*
  • Epoxy Compounds / chemistry*
  • Kinetics
  • Pyridines / chemistry*
  • Structure-Activity Relationship

Substances

  • Alkanes
  • Chromogenic Compounds
  • Epoxy Compounds
  • Pyridines
  • 4-(4-nitrobenzyl)pyridine
  • DNA
  • Deoxyguanosine