REACTION OF MUCOCHLORIC ACID WITH ADENOSINE - FORMATION OF 8-(N-6-ADENOSINYL) ETHENOADENOSINE DERIVATIVES

The bacterial mutagen mucochloric acid was reacted with adenosine in a queous solutions at 37 degrees C. In the HPLC chromatograms of the rea ction mixtures two peaks of unidentified products were observed at lon ger retention times than the previously characterized ''etheno'' and ' 'ethenocarbaldehyde'' adducts. Following isolation and purification wi th chromatographic methods, the products were characterized by UV abso rbance, H-1 and C-13 NMR spectroscopy, and thermospray mass spectromet ry. 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.