Adducts of chlorohydroxyfuranones and of aldehyde conjugates

The work reported here concerned the structural determination of adducts formed in reactions of nucleosides with chlorohydroxyfuranones and with conjugates of malonaldehyde and acetaldehyde. The chlorohydroxyfuranones are bacterial mutagens produced during chlorine disinfection of drinking-water, malonaldehyde is the major end-product of lipid peroxidation, and acetaldehyde is the major metabolite of ethanol. Exogenous sources of acetaldehyde are, for example, tobacco smoke and automobile emissions. The chlorohydroxyfuranones were found to form substituted and unsubstituted cyclic etheno adducts with adenosine, cytidine and guanosine and substituted cyclic propeno adducts with adenosine. The malonaldehyde-acetaldehyde conjugates reacted with adenosine to produce a strongly fluorescent dihydropyridine purine derivative and a substituted propenoformyl adenosine derivative. Most of the adducts identified in this study are new, and their mutagenic properties are as yet unknown.