Reaction of acrolein with 2'-deoxyadenosine and 9-ethyladenine--formation of cyclic adducts

Bioorg Chem. 2006 Feb;34(1):39-48. doi: 10.1016/j.bioorg.2005.10.006. Epub 2005 Dec 15.

Abstract

Treatment of 2'-deoxyadenosine with acrolein at pH 4.6 in 37 degrees C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2'-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products, 3E and 4E, were structurally characterised by UV, mass spectrometry and NMR spectroscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrolein / chemistry*
  • Adenine / analogs & derivatives*
  • Adenine / chemistry
  • DNA Adducts / chemistry*
  • Deoxyadenosines / chemistry*
  • Hydrogen-Ion Concentration
  • Models, Chemical
  • Spectrum Analysis
  • Stereoisomerism

Substances

  • DNA Adducts
  • Deoxyadenosines
  • 9-ethyladenine
  • Acrolein
  • Adenine
  • 2'-deoxyadenosine