AZULENE/ALDEHYDE ASSOCIATION: AN ANALOG FOR DAMAGED DNA DETECTION

Abstract

Loss of a nucleic acid base from DNA can leave behind a reactive aldehyde group on ribose. To detect the presence of such “abasic sites,” ethyl-2-aminoazulene-1-carboxylate, a novel azulene-based analog of guanine/adenine, was synthesized. Valeraldehyde was chosen as a simple model for an abasic site. 1H NMR kinetics studies with ethyl-2-aminoazulene-1-carboxylate and valeraldehyde show that this is a slow reaction and suggest that it is zero-order with respect to valeraldehyde. This is consistent with a complex mechanism.