Reaction of acrolein with 2′-deoxyadenosine and 9-ethyladenine—Formation of cyclic adducts

Acrolein forms two cyclic adducts with the adenine base in aqueous solutions. One adduct is an unstable acetal consisting of two condensed rings derived from two units of acrolein. Treatment of 2′-deoxyadenosine with acrolein at pH 4.6 in 37 °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, 3 E and 4 E , were structurally characterised by UV, mass spectrometry and NMR spectroscopy.