Formation of the cyclic 1,N2-glyoxal-deoxyguanosine adduct upon reaction of N-nitroso-2-hydroxymorpholine with deoxyguanosine

Abstract
N-nitroso-2-hydroxymorpholine, a mutagenic metabolite of N-nitrosomorpholine and N-nitrosodiethanolamine, reacted with deoxyguanosine at pH 7, 37°C, to give 3-(2-deoxy-β-D-erythropentofuranosyI)-6, 7-dihydro-6, 7-dihydroxyimidazo-[1, 2-a]purine-9(3H)one, which is also formed by reaction of deoxyguanosine with glyoxal. The results suggest that this adduct might be involved in DNA binding by N-nitrosomorpholine and N-nitrosodiethanolamine.