Reaction of mucochloric acid with adenosine: formation of 8-(N6-adenosinyl)ethenoadenosine derivatives.

Abstract

The bacterial mutagen mucochloric acid was reacted with adenosine in aqueous solutions at 37 degrees C. In the HPLC chromatograms of the reaction mixtures two peaks of unidentified products were observed at longer retention times than the previously characterized "etheno" and "ethenocarbaldehyde" adducts. Following isolation and purification with chromatographic methods, the products were characterized by UV absorbance, 1H and 13C NMR spectroscopy, and thermospray mass spectrometry. The products were found to consist of ethenoadenosine derivatives which bonded an additional adenosine unit to C-8 in the etheno bridge. In one of the products a formyl group and in the other an oxalo group was localized at C-7 in the etheno bridge. The yield of the products was about 0.04 mol% (calculated from the original amount of adenosine) in the reaction mixture held for 4 days at pH 7.4. It was concluded that mucochloric acid acts as an oxidative agent during the course of formation of the products.